The Sandwich Generation Survival Guide

You asked. We answered.

Gray Monster’s Kim Elliott takes over The Sandwich Generation Survival Guide to bring real, unfiltered answers to your most pressing questions. She puts host Candace Dellacona in the hot seat, where Candace draws on her experience in elder law to tackle hundreds of reader-submitted topics—nothing off limits.

From estate planning and elder law basics to caring for aging parents, family conflict, and how to have difficult conversations, this episode delivers practical guidance for adult children navigating the realities of caregiving.

No legal jargon. No sugarcoating. Just clear, actionable advice for the sandwich generation—those balancing their own lives while caring for older loved ones.

If you're searching for help with:
  • Aging parent care planning
  • Estate planning tips
  • Family caregiving challenges
  • Managing stress as a caregiver
  • Navigating difficult family dynamics
This episode is built for you. Listen now to get the insight and real-world strategies for surviving—and thriving—in the sandwich generation!
 
  • (00:00) - Episode Intro
  • (01:09) - What Is Gray Monster
  • (02:52) - Updating Wills After Loss
  • (05:43) - Probate Basics And Trusts
  • (09:31) - Starting The Hard Talks
  • (11:51) - Sibling Conflict And Will Access
  • (15:18) - Dementia And Signing Documents
  • (16:41) - POA And Healthcare Directives
  • (18:20) - Medicaid Planning And Resources
  • (21:45) - Elder Law Vs Estate Planning
  • (23:07) - Protecting Parents From Scams
  • (26:43) - POA Versus Joint Accounts
  • (27:38) - Estate And Inheritance Tax Basics
  • (29:57) - Estate Income Returns
  • (30:06) - Executor Misconduct Accounting
  • (32:36) - Bonds and Court Remedies
  • (33:29) - Will Contest Deadlines
  • (34:36) - Caregivers and Fiduciaries
  • (36:33) - Second Marriage Inheritance
  • (40:33) - Prenups and Health Proxies
  • (42:51) - Minimal Plans Advance Directives
  • (43:43) - Nursing Home Bills Liability
  • (45:06) - Estate Debts and Creditor Order
  • (46:43) - Medicaid Clawbacks to Children
  • (47:54) - AI and Online Legal Forms
  • (51:54) - Out of State Executors
  • (53:02) - Death Certificates and Digitizing
  • (55:41) - Trust Funding Basics
  • (56:58) - When Parents Need More Care
  • (58:26) - Wrap Up and Subscribe
 
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Disclaimer: The content presented in this podcast is for general understanding and informational purposes only and is not intended to provide legal advice, nor should it be construed as legal advice. The information provided is based on general legal principles and may not reflect the current state of the law or specific details of your case. Laws vary by jurisdiction, and legal outcomes can be highly dependent on the specific facts and circumstances involved. Listening to or using this podcast does not create an attorney-client relationship between the hosts, guests, or participants and any listener. It is your responsibility to seek professional legal advice for your specific situation from a licensed professional attorney in your state.

Creators and Guests

Host
Candace Dellacona
Principal, Offit Kurman
Producer
Eric Kovac
Creative Team Manager, Offit Kurman

What is The Sandwich Generation Survival Guide?

Welcome to The Sandwich Generation Survival Guide, where we explore the challenges and strategies of navigating life caught between work demands and supporting our loved ones while maintaining our own well-being. Join us in this dynamic podcast series as we uncover the complexities individuals face balancing multiple roles in the modern world. Our host, Candace Dellacona, shares personal experiences and professional insights to guide listeners through this complex journey.

Gray Monster Takeover: Essential Estate Planning Tips for the Sandwich Generation with Candace Dellacona
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Episode Intro
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Kim Elliott: Hi survivors. This is Kim Elliott with Gray Monster. We're switching it up this week. I am taking over the Sandwich Generation Survival Guide, and I'm stepping in for Candace and asking her all the questions you have about supporting your aging parents.

Candace Dellacona: Welcome to the Sandwich Generation Survival Guide. I am your host, Candace Dellacona, and as you heard, we're doing something a little different today on the Sandwich Generation Survival Guide. My guest is Kim Elliott, who many of our listeners already know, but for those who don't, Kim is the founder of Gray Monster, the free weekly newsletter that has become a lifeline for adult children navigating the often overwhelming world of caring for our aging parents. Welcome, Kim.

Kim Elliott: Hi, Candace. Thanks for having me.

Candace Dellacona: So excited to have you here and to do something a little different today on this episode.

What Is Gray Monster
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Candace Dellacona: For those who don't know about Gray Monster, tell us what it is, how you came to find it, and how our listeners can subscribe.

Kim Elliott: Yeah, absolutely. So Gray Monster is a free weekly newsletter delivered Sunday to inboxes all over the US. To really, I would say Millennials, Gen X, anyone supporting their aging parents as this role shift occurs. And really the name originates from just that, right? There's a lot of ambiguity as roles start shifting, as adult children start giving the care that we once received to their own parents.

And I think there's a real fear in that. And so we're addressing that fear head-on with a little levity, and always respect and, a lot of dignity. And always getting to talk to experts like you and sharing it with our community, so I'm thrilled to be here.

Candace Dellacona: Yeah, I love it. And, you touched on the name. I think that's a perfect way to frame it. There are so many things to cause us anxiety and instills a lot of fear, both for our parents, I think, and for us. And part of the episode today is hopefully to assuage some of those fears. You kindly reached out to your readers , and you asked for their requests to find out what they want answers to. So without further ado, I'm gonna turn The Sandwich Generation Survival Guide over to you, my friend, and you can start with the questions that Gray Monster came up with. Let's go.

Kim Elliott: Yeah. So we played a little game in last week's newsletter called Ask the Attorney, and we received a ton of responses. Hundreds of people wrote in with questions that they have specific for you. Some are a little juicier than others, but I will jump right into it.

Updating Wills After Loss
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Kim Elliott: Right off the bat, do wills have to be updated after a sibling dies? This reader said no, but her mom disagrees. What's your guidance?

Candace Dellacona: Well, first of all, I'm so sorry for that writer that they have lost a sibling. I know how hard it is, and things like that make it even more complicated when you have an aging parent. Generally, the answer is any time a beneficiary or someone in the family unit passes away, estate planning documents should be reviewed. And the reason why they should be reviewed is because if a sibling passes away and that sibling does or doesn't have children, there's a good possibility that it will impact what that sibling's child or children will receive, and we have to make sure it's reflective of what the surviving-- You know, the parents would want for the surviving grandchildren or the next of kin.

So I think the answer is kind of in between. Maybe Mom is right and maybe the writer is correct in that at least we can take a look at it. You may not have to change it, but definitely review it.

Kim Elliott: So walk me through that a little bit more. Are grandchildren, I would assume, like in this particular instance, are they often included in wills or is it really just like up to the parent of the grandchildren to decide what that looks like?

Candace Dellacona: That's a great question, Kim. Often documents like wills and trusts which leave assets to people upon passing. If a document says, "I leave everything to Candace," and I die, and it is my parent leaving it to me, then automatically, in most states, my children would step into my shoes and inherit what I would have received. However, there are some opportunities for people to draft their documents differently. They may not want their grandchildren to get their parents' share. Maybe the document is drafted to say, "To only my surviving children," so the grandchildren would never inherit, that it's only going to the surviving children.

So, that's why it's really important not to assume that it's one way or another, so you can draft differently, and sometimes there are state laws that direct it. So, check with your local counsel.

Kim Elliott: Okay, so in this case, would they have to go to the same attorney who drafted it, or could the adult child go to an attorney they know and trust?

Candace Dellacona: The attorney should be the attorney for the parent because it's the parent estate planning document. But you don't have to go to the same lawyer, but you should go to a lawyer who is barred in the state where you reside. So if mom and dad live in the state of New Jersey, you should go see a lawyer who is licensed to practice in the state of New Jersey, their state of domicile.

Kim Elliott: Okay. Got it. Perfect.

Probate Basics And Trusts
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Kim Elliott: That actually is a great segue into the next question. How important is it for adult children to familiarize themselves with the laws of the state that their parents live in and will likely pass away in? Really this particular reader was like, "I just wanna avoid probate after death." And that's the P word. A lot of people wrote in about probate. Maybe you could, like what is it?

Candace Dellacona: Yeah, let's talk about that. It's great point, Kim. So probate is something that people say constantly that they want to avoid without even really knowing necessarily what it is, right? So probate is the process of proving that somebody is dead, proving that the document they signed, like a will, is appropriate and meets the metrics of the state requirements.

So for example, often wills have to be written. They cannot be oral wills. It has to be a document, it has to be signed, and it has to be witnessed. Witnessed meaning people watching you sign your documents. You also have to prove that the person who signed the will had the mental capacity to sign it at the time.

So some states, there's an automatic presumption that the person did have the mental capacity, so you don't have to prove anything. Somebody would have to disprove. So that process takes a while because after the document is acknowledged as, "Okay, this looks like a legitimate will," then the next step is the court saying, "Who did you name as executor? Is this person appropriate? Is this person able to handle this type of task?" And then the executor is appointed. So you naming a person as an executor in your will is really just a suggestion. So probate encompasses that whole process, proving death, proving that the document is good, and proving that the person that you've appointed as executor is the right choice. And people want to avoid it.

Kim Elliott: Yeah, because it's just more work. And so how do they avoid it? A will's not gonna avoid that, correct?

Candace Dellacona: Correct. That's right. So in most states, you can avoid the probate process by using a trust instrument instead of a will. So a trust is what we call a will replacement. It does not have to be authenticated, quote unquote, by a court. A trust names a successor trustee that automatically has the requisite authority when you die, so they don't have to go to court to have anybody appoint them, and that's why probate can be avoided.

The other thing about probate, Kim, is that in most states it takes a long time, 'cause think about all of the things that the court has to do times all of the people that have passed away, right? And it's expensive. So having a trust really does away with the probate process and makes things go a lot quicker upon somebody's death.

Kim Elliott: Okay. I've heard some states have a bit of a workaround where it's like not full probate, but then not a trust in place. Is that accurate?

Candace Dellacona: Yeah, so there are states that have amended proceedings, what we call shorter proceedings, but often those shorter proceedings are related to assets that are not worth very much money. So usually there's this, a threshold, a cutoff if you will, $30,000, $50,000. If you die less than X amount of dollars, then you don't have to go through a full probate proceeding.

But for the most part, even if you don't have a will, you have to go through what they call an administration proceeding, which is the same thing, saying, "Who should be in charge of distributing your assets? What are your assets?" And making sure that the assets end up with whomever the state law says if you don't have a will. So having a trust wipes away having to go through that whole court proceeding.

Kim Elliott: Okay.

Starting The Hard Talks
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Kim Elliott: I know that our readers often ask about, "How do I talk to my parent about, have these conversations?" Because again, to the point of, there's a lot of fear involved. If I put myself in my parents' shoes or any older adult, I'm like, "I'm not totally sure I want my adult kid up in this mix," right? I don't know what I'm willing to share.

And I think that's one of the things that Gray Monster really works to do, and what you're doing with your podcast is hey, we gotta have some of these conversations before a crisis, right? What is your recommendation? How do we blame the attorney so that parents wanna talk to adult children?

Candace Dellacona: Listen, I'm always happy to be a buffer. And, as I say to clients or their adult children, "I don't have to celebrate Thanksgiving with you." I'm happy to be the bad guy and come in more like gangbusters than you can.

But, taking a step back, I think it's really important that you think about why the conversation is hard to have. You're saying words out loud to an aging parent who may or may not be in touch with the fact that they're getting older or they have limitations. They could have cultural beliefs or religious beliefs that have them deal with those issues quite differently, and I think it's really important to take stock of all of those things before you start the conversation. I also think it's really important when you start the conversation that it not be during a heightened period of something terrible happening.

Kim Elliott: Right.

Candace Dellacona: Taking a step back and starting from a place of love, or at least, at the very least, respect.

Kim Elliott: Yeah, absolutely.

Candace Dellacona: Yeah, it's really hard though, because, look, I have been an adult child in this situation, an adult niece, and looking at a person that you love and saying, "I think you have limitations," or, "You could have limitations," or, "This is what I think is happening," is really hard to do. So I do not, say this flippantly or lightly at all. I also want to point out, Kim, it doesn't have to be one conversation.

Kim Elliott: Yeah.

Candace Dellacona: You can have small interjections over the course of time about these different issues. It doesn't have to be one big family meeting where you're sitting there and addressing every single issue that could possibly come up.

Kim Elliott: That's such a great point. I agree that making sure the moment feels right and oftentimes it's several conversations, it's not just one makes good sense.

Sibling Conflict And Will Access
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Kim Elliott: Talk to me a little bit, because I had some readers write in about "Hey, my sibling isn't in the will, but they don't know about it." Or " Our mom doesn't want them involved." What do you recommend then?

Candace Dellacona: So look, family conflict is part of it. Family conflict is part of our daily existence, so why wouldn't it be part of an estate plan? Why wouldn't it be part of what happens when somebody ages? Now, I think what's really important to keep top of mind, and I do this all the time in my practice, is remembering who's in charge. So when you think about an estate plan when it comes to a sibling being a beneficiary or not, it's not up to anyone other than the parents who's in the estate plan.

Kim Elliott: Yeah

Candace Dellacona: And at the same time, I recognize that if an estate plan is not made known to everyone in the family, sometimes the siblings who are disinherited don't find out until after mom and dad are dead, and the siblings are left holding the bag.

Kim Elliott: Yeah, so we got a question about that actually specifically and I'm gonna pull up our list here. But does the executor let's say the parent passes away, does the executor, assuming it's a sibling, do they have to physically share the will with their siblings, assuming they have siblings, or anyone in it?

Candace Dellacona: That's a great question. Most states, Kim, and again, I am not licensed to practice in every state, so I'm gonna remind everyone that this is not legal advice, that you should go to your own lawyers in your own states. But I will speak in general terms to say that in most circumstances, wills are public documents and those who are named in a will are entitled to a copy, and those who are next of kin are entitled to a copy of the will.

Kim Elliott: When you say it's a public document, can I just go on my local county courthouse and read them? Or how-

Candace Dellacona: Yes.

Kim Elliott: Really?

Candace Dellacona: And in fact, many New Yorkers will remember when the great James Gandolfini passed away from The Sopranos, a copy of his will was on the cover of the New York Post.

Kim Elliott: Wow.

Candace Dellacona: So wills are public, very public. Anybody can go to the courthouse and read a will. It is very rare that they are under seal, and that is why many people, public-facing people, choose trusts over wills.

But I do want to go back to the sibling thing, Kim, because I think one of the things, I've been practicing 24 years, and that's always a conundrum that's presented in many different forms over the last two decades. And what I'll tell you is that the best advice I give to adult children and their parents, and hopefully their parents, is if there is a distribution where it's unequal among siblings or if one sibling is totally left out, I tell the parents, "You know what? You should write a letter of intent." It's a letter that explains

explains what their thought process was in making an unequal distribution. The letters are not shared until after mom or dad or both mom and dad pass away, and it gets the other sibling off the hook so that

Kim Elliott: Yeah

Candace Dellacona: the fracture does not get worse between siblings.

Kim Elliott: Yep. Yeah, that's such a great point, and hopefully if they are leaving resources, there's enough to cover some therapy for, a letter left by your deceased parent.

Candace Dellacona: Therapy fund. Yeah, I love it.

Kim Elliott: Exactly.

Dementia And Signing Documents
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Kim Elliott: Okay, I wanted to back us up even a bit further. When we were talking about getting these documents signed one of our readers asked, "Does a dementia diagnosis prevent legal docs from getting signed?"

Candace Dellacona: I love that. Yeah, I love that question.

Kim Elliott: Let's say adult son sitting with dad in a doctor's office gets a diagnosis. It's still early, but they don't have the documents in place. Can they even get them in place now?

Candace Dellacona: So many people have that question, Kim, so it's not surprising at all that one of your Gray Monster readers had it. Believe it or not, the threshold to sign a will in most states is very low. In fact, there is language in a lot of our case law saying that even if you have a moment of lucidity, if you sign your will in a moment of lucidity, that is sufficient. Now, not every state is exactly the same, but there's a public policy behind the fact that many people are clear about who they love and who they want to inherit from them, even in a time of memory impairment with dementia or Alzheimer's. Now, that's not to say that if a parent thinks that it's 1974, they can sign a will. But having a diagnosis does not preclude someone from signing a will. But I will tell you that the threshold to sign a power of attorney is usually higher than signing a will.

POA And Healthcare Directives
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Kim Elliott: Okay, so then let's go there because there were a lot of POA questions. There's power of attorneys, there's living wills, there's advanced directives. Let's break those down really simply so the Gray Monster reader and the podcast listener knows what's what.

Candace Dellacona: Yeah, yeah. So power of attorney is the document for finances. That is the document in which the principal, mom, dad, senior person says, "I appoint Kim as my agent to make financial decisions for me." And the power of attorney can usually be customized to bestow certain powers and withhold certain powers. So you may give a really broad power of attorney because you trust Kim, and you want to make sure that anything that you could do, you want Kim to be able to do. You can also create what we call limited powers of attorney. So it really depends on what you're looking to do.

Kim Elliott: OK

Candace Dellacona: And then there's the healthcare side. Some states call healthcare documents a power of attorney for health. Some states call it healthcare proxy. Some states call it an advanced directive. Whatever you want to call it, it's similar because you're appointing a person to make healthcare decisions for you when you are no longer able to make those decisions for yourself. So a power of attorney for finances has nothing to do with health and is only finances, and a healthcare directive or a healthcare power of attorney only has to do with healthcare decisions.

Kim Elliott: Okay.

Medicaid Planning And Resources
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Kim Elliott: We had a few questions around keeping a parent in place while receiving in-home care for, again, an Alzheimer's or dementia diagnosis and then figuring out how Medicaid fits into all of this. You hear a lot about the Medicaid clawback and how far back they look. Is this where we get a financial planner involved? Is this where we get an attorney involved? Is this where we get both involved? What's your guidance here?

Candace Dellacona: So it's really important to have a team, and if you have a financial advisor or someone that is more financially minded, it's always great to get them involved. And oftentimes an elder law attorney in your local state can be helpful too, because the Medicaid process is a tricky one.

For our listeners out there, Medicaid is a federal program. It's instituted by the federal government. It was passed in 1967 at the same time Medicare was. To distinguish between Medicaid and Medicare, everybody gets care at 65. Not everybody gets aid, Medicaid. Medicaid is means tested, meaning they look at how much income you have and how many assets you have. So while it's a federal program, listeners, it is implemented at the state and the county level, so it is wildly different from state to state. It is very possible that you live in a state where Medicaid could provide you some benefits, whether it's receiving care at home, like a home care attendant to come in and make sure that, your medications are all laid out for you and that you're safe in your home and your home is clean, and it could even cover institutional care like a nursing home. And some states even have assisted living facilities that accept Medicaid as a form of payment. But it really is different state to state.

Kim Elliott: So do you think the best place to start that process if you're the adult child or you're the caregiver in this situation is to go to a local you're looking at elder care locator, you're trying to find somebody locally? Where do you think somebody should start understanding that, hey, there's only X amount of resources? We of course don't know how long, Mom's gonna live.

Candace Dellacona: You're right, Kim. I think one of the most important things is where you start, because you don't want to waste these precious resources by going down a path that could be an expensive mistake.

So I always say go to the actual source. The best place to start is your local office on aging in the county in which you reside. That is free for everyone. Often they have social workers that can point to your local resources about those local resources. The other thing that you can do is if you have a loved one with memory impairment and a diagnosis of dementia or Alzheimer's, for example, there is a program under Medicare that not a lot of people know about called the GUIDE program.

And the GUIDE program, you have written about it, Kim, in Gray Monster. That was a great newsletter. I loved it because it really goes into what the GUIDE program can do, which is exactly this: provide local resources like elder law attorneys that know what they're doing and can help you with the quagmire that is Medicaid.

Kim Elliott: Yeah, and look my hot take on GUIDE is it's a start. I think there's a long way to go, and by no means does it in its current state cover the amount of care needed when we're talking about a dementia diagnosis, but it's certainly a start.

Elder Law Vs Estate Planning
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Kim Elliott: You keep using the term elder law attorney. Break it down for Gray Monster readers. What's the difference between a elder law attorney and an estate planner?

Candace Dellacona: Yeah. So that's a good question, and thank you for bringing that up. I often forget that people don't realize. So trust and estates lawyers, that's a really broad category. We talk about all things like dying and disability and setting up documents, whether it's trusts or wills or what have you. An elder law attorney is a subspecialty under that umbrella that also knows about, in addition to wills and trusts and powers of attorney, also knows about public benefits like Medicaid or like the Aid and Attendance program if you're a veteran, or, geriatric care managers.

So it's just like an extra feature that we are aware of based on our clients and knowing what our local resources are.

Kim Elliott: So did you have to go through extra training for this?

Candace Dellacona: So I actually didn't. There is a certification. You can become a certified elder law attorney and it is a really sort of prestigious certification. So certainly if you have one in your area, look them up. There's the National Academy of Elder Law Attorneys. But for those of us who have been practicing for a long time in this area, we work really hard to stay up to date on those local resources and to stay up to date on the Medicaid rules, which are changing fast and furious these days.

Kim Elliott: Yeah, indeed.

Protecting Parents From Scams
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Kim Elliott: I wanted to go down this path of some of these questions or some of the readers have asked really around protecting the person that you're caring for and supporting. That's so big, right? One of the things that Gray Monster believes deeply in is agency while aging, and that's tough when these roles start to shift.

And I want to protect agency for both parties, right? The caregiver and the person receiving the care. You hear about romance scams. You hear about the Bitcoin ATM all the time. What can the caregiver do to protect their, parent or older adult who they're caring for to not only educate them on these scams that are out there, because unfortunately people love to scam older adults.

And then secondly, when exposed to a scam what is the first thing-- I mean, is there a top three, like immediately do these three things when you find out there's been potential exposure?

Candace Dellacona: So there are different types of scams. I think that, what is important to decipher between is the emotional vulnerability that your aging loved one may have that can make them more susceptible to a financial scam which we're seeing quite a bit. I think one of the things that makes our aging population more vulnerable to that is there are a lot of solo agers, Kim, meaning people that are growing old away from their family of origin or they don't have a family of origin or it's very small.

So when it comes to these scams, I think if you are the advocate for the aging loved one, I think the things that you need to look out for are, number one, isolation. Is that person pulling away from you? Are they not answering the same amount of questions? Are they bringing up someone in conversation that you hadn't heard of before and it seems like they're around a lot and you're not able to have independent conversations with them? Those are like the telltale signs.

If something has actually transpired, so let's say it's further down the line, Kim, and you look at a bank statement and you realize money is gone. What do you do? The first thing you do is you notify that banking institution of a possible fraudulent issue or fraudulent activity. If it's an identity issue, you actually can go through the FTC, the Federal Trade Commission. There is an entire site on identity theft or thefts such as these. But back to the institutions, there is a rule under FINRA that says banks are supposed to know their customers. They're supposed to know if they're elderly and vulnerable. So if you feel like your parent is particularly vulnerable, go to the bank with them with the power of attorney. Let the local branch know that you want some guardrails set up around accounts to make sure that these wire transfers that are happening to foreign countries, that things like that are prohibited on these accounts of our vulnerable older loved ones.

So that's where I would start if something happened. And then of course, filing a police report. Even if the police are resistant and, listen, I think a lot of police are overwhelmed with the amount of work they have to do certainly, but sometimes police are reluctant to make a report, but you have to advocate and make sure that a report is made so that when you dispute it with your bank you have a backup police report so that you can get some money back if that's possible.

Kim Elliott: Yeah that's good guidance.

POA Versus Joint Accounts
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Kim Elliott: When you talk about going to the bank, I hear a lot about "Oh, well, I'm on my mom's account," or, "I'm on my dad's account, that's good enough." But that's not the same as a POA, correct?

Candace Dellacona: It's not. And I think one of the things that you should think about too is being on an account can have several different definitions. You can be an authorized signer, you can be an owner, you can be a POA. If you are on a bank account as an authorized signer, that's great for that account, but what about everything else in your aging loved one's life?

What about signing a tax return? What about making sure property taxes are paid or advocating in an insurance claim? So having the power of attorney isn't just about the actual finances, it's anything related to the person's worldly goods and their sort of place in the world as it relates to all institutions. So the power of attorney does a lot more than just give you access to a bank account.

Estate And Inheritance Tax Basics
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Kim Elliott: Yeah, so we received a question actually regarding taxes specifically. And one of the readers wanted to know, their dad had passed away, and they said because inheritance tax, because the value of the estate isn't over, some amount, like they don't have to fill out a tax return.

And there's no, it's the IRS, it would take forever for the IRS to come find them if they didn't, so like their sibling was like, "You don't have to worry about filing a tax return." I know you're not a CPA, but any guidance here?

Candace Dellacona: I'm not a CPA, you're right, Kim, but we do deal a lot with taxes in my area of law. So what I'll say is this: when you pass away, in every state there is a different rule about the dollar amount that you can pass away with, and if you don't hit the threshold of it being a quote-unquote taxable estate, then it might be true that you may not owe estate tax. But there are some states that also have something called an inheritance tax, so the person receiving an inheritance may have to file to advise your, New York State, for example, or New Jersey, that you're receiving money. Now, New York, we do not have an inheritance tax, but other states do. But I will also say that when somebody passes away, oftentimes the estate has to file an income tax return, Kim.

So when you and I file the income tax, we know what to do. But they treat the estate as a person for income. So if an estate earns more than, I think the threshold is $600, so between the time the person passes away until the assets are totally distributed out of the estate, did the estate earn $600? If so, you have to file an income tax return for the estate. That's not the same as an estate tax return.

Kim Elliott: Okay. Is that including selling the house, selling dad's car, is that part of the $600 or does that make up part of the $600?

Candace Dellacona: So the $600 is the threshold for income earned on the estate. So let's say, for example, you have Apple stock and you die February 1st. If the estate is not distributed until September, did the Apple stock earn more than $600 in income?

Estate Income Returns
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Candace Dellacona: If so, we'll have to file an income return for the estate, which is different than the estate tax.

Kim Elliott: Okay. Okay. Helpful.

Executor Misconduct Accounting
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Kim Elliott: We had another reader reach out and it sounds like they had uncovered some questionable or nefarious sibling behavior who was the POA while their dad was alive, and then executor of his estate after his passing. And it had been uncovered after the passing that he had been using his dad's bank account as his own prior to his death, and then after his passing, had taken more than he was entitled to from the distribution. What does the sibling do?

Candace Dellacona: That is such a difficult position for that reader to write in about. So I can only imagine, how painful that is on every level, and unfortunately it happens. I think there are two different issues here. There's the issue of what the sibling did before the parent passed away,

Kim Elliott: Mm-hmm.

Candace Dellacona: and what fiduciary obligation they may have breached before the parent passed away and then after. With respect to the estate, which is after, with their role as executor, there are proceedings in every state that will allow another beneficiary, another sibling, to request an accounting. And what that means is, if you're a beneficiary of an estate and you think that something is amiss, you have the right to demand an accounting, and it's actually asking the court to have the executor comply and show them all of the records to reflect what's transpired financially in the estate to figure out how that person came up with whatever distributions were made to himself or herself.

With respect to the power of attorney, oftentimes those issues are brought into the estate because people sometimes pilfer assets before people pass away, and it's not discovered usually until after.

So sometimes local jurisdictions will entertain issues before death and after death. But it is really hard, and I think the question for a lot of people becomes, "Do I say anything, and what's gonna happen to my relationship with this sibling?" And listen it's a question that most of us can't answer for other people. I think it depends on how far you are willing to take it and how far you're willing to press.

Kim Elliott: Yeah. So how do states or counties handle that? Is it after the accounting has been done, if they've recognized that there was something unsavory that occurred.

Candace Dellacona: Yeah.

Bonds and Court Remedies
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Candace Dellacona: If something transpired and the executor either took too much or, made an error even, a court, a judge will order that the executor return those funds to the estate and redistribute them to the right person. Sometimes, Kim, when executors are appointed, they also have to file a bond, which is like an insurance policy, so that if the executor doesn't do the right thing, at least the bond is there to cover any damages if money is already spent. Now, it's not all that common for judges to require that executors file bonds, especially if it's in a family situation. But, there are jurisdictions that require bonds, so that could be an extra layer of protection in the event that somebody took money and it's spent and it's no longer there, perhaps you have the bond you can go after.

Kim Elliott: Oh, that's so tough.

Candace Dellacona: It is.

Will Contest Deadlines
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Kim Elliott: Is there a statute of limitations on contesting a will?

Candace Dellacona: Yeah, and it's different for every state. In general what you have to think about is that most states don't want that period to go on forever because there is a public policy to settle an estate and move on. So it's really important that you find out in your local jurisdiction how much time you have to contest a document.

And sometimes it's not a some certain amount of time. You're given a document, and if you, what we say, waive your right, you could even be ending the statute of limitations earlier. So if you have, let's say, nine months to contest in any jurisdiction and you receive a waiver saying, "I'm good. I think everything that the executor is doing is kosher and all set," then you could be giving up your right to contest an estate.

So make sure that if you're a little nervous about the person who's appointed, if you want some oversight, seek your own counsel so that you can have a lawyer to advocate for your position to make sure everything is done the right way.

Caregivers and Fiduciaries
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Kim Elliott: So we talk a lot about the familial connection. Oftentimes it's a paid caregiver that is supporting an older adult. Do you recommend that a paid caregiver have these legal documents, or is it a case-by-case basis? And if there is, unsavory behavior that occurs, is that where it becomes a crime? Talk us through that a little bit.

Candace Dellacona: Yeah. I'll just say that most of the fraud that sort of happens in our area, Kim, as it relates to seniors, is usually perpetrated by family members, not paid caregivers. It's much more common to have fraudulent activity by an adult child. So that's first. Second, there are certain circumstances where people have small families, and perhaps they don't have family members that can step into the role as power of attorney or healthcare proxy. So there are certain circumstances in which a person may appoint a paid agent in that role. There are daily money managers that will fill in the role as trustee or power of attorney. They're licensed, and they often have insurance policies to guarantee their fiduciary obligation to you.

Likewise, when you think of healthcare, you can pay a healthcare advocate to serve in your role as a healthcare power of attorney or a healthcare proxy. Sometimes your own physician will fill that role if you ask them to.

So there are certain circumstances where, yeah, there can be professionals in those roles but I wouldn't automatically assume that they are more susceptible to fraudulent or unscrupulous activity.

Kim Elliott: Yeah, that, that's good insight. Thank you. Worth noting the sirens that were going off in the background of your office, unpaid actor during this particular topic.

Candace Dellacona: Perfect timing.

Kim Elliott: Certainly timely.

Second Marriage Inheritance
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Kim Elliott: A few more questions we've got from some folks really around stepparents, stepchildren, like including in wills, not including in wills.

One reader wrote in and was like, "Look, my mom just remarried at 85. Does her new spouse automatically inherit everything? Are his kids going to receive part of the inheritance? What do we do?"

Candace Dellacona: Modern family issues, Right. People are living longer and so second marriages, third marriages are so much more common than they used to be. And with that, you have these sort of additional layers of complication. And to your point, stepchildren, stepparents, how do they fill in those roles?

And, what I'll say is, and I'm sorry, it's the perfect lawyer answer, but it depends, right? So there

Kim Elliott: is the perfect lawyer answer.

Candace Dellacona: Y- yeah. So there are certain states that require that if you're married to someone, you have to leave them a threshold amount or percentage of your estate. In New york, if

Kim Elliott: Even if it's not in the will?

Candace Dellacona: Yeah. Yeah, there's a public policy to not leave a spouse behind impoverished. And so in New York, we have these requirements that you cannot totally disinherit your spouse unless there's a prenuptial agreement or a postnuptial agreement whereby the spouse who is disinherited acknowledges it and says, "I'm okay with it." For these readers' questions that are asking about stepparents, it really depends on the jurisdiction where your parents are located. And, I think it's even more complicated, Kim, because when you talk about an 85-year-old who is getting remarried, likely the 85-year-old had a whole different life, likely with another spouse, with other children, with assets that were acquired during that first or that second marriage if they're on the third. So it's really important that those parents who get remarried either do a prenup or have a really good lawyer that drafts estate planning documents that will keep those assets outside of the grasp of the stepparent or the stepchildren.

Kim Elliott: Because if there was a will prior, where does that come into play upon death, assuming the second marriage, they're married at death?

Candace Dellacona: Think about it this way. If the step-parent and your parent got married and your parent had a will before they were married and your local state says you have to leave something to your spouse and you don't change your will, the court will change the will and make sure that whatever the statutory requirement, whether it's a third or a half or whatever it is, that it's met. So it's really important that when you enter into a second marriage and you have kids from the first or you have different beneficiaries from your new spouse, that you have an open and transparent discussion about expectations. I think this really becomes important, Kim, when there's cohabitation. And what I mean by that is often when we get married, we live with our spouses, right?

And if you have two spouses who came into the marriage having had a whole life before the second or this third marriage, if one spouse is moving into the other spouse's home and the spouse who owns the home dies before the other spouse the non-homeowning, spouse, what do they do?

Do they have rights to stay there for a certain amount of time? If so, how long? And what about the contents? Maybe all of your photo albums or your late mother's belongings are still in that house. Do you have a right to go into that house? How long can your step-parent remain in that house? So these are really uncomfortable topics, but even more uncomfortable if somebody passes away and you're left with this really unfavorable result.

Kim Elliott: Yeah.

Prenups and Health Proxies
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Kim Elliott: So really, you are, as most lawyers are, like, you're a proponent of buttoning this up before any of these things happen. And I think a lot of people have questions around the prenuptial, postnuptial agreement. There's this thing going around on the internet like, hey, every state you get married in has a prenuptial agreement. It's just it may not be the terms that, you realized you were signing up for.

Candace Dellacona: Yeah, I think that's really true. That particularly with second marriages, I think prenups and postnups become even more important, and local jurisdiction can really dictate what you can contract against or for. So it's so important that you get the proper legal counsel to do that. Like I said, it's so much more common to have second and third marriages when people are living till 100 years old, right? And I think as the human condition is, we wanna pair up. It's nice to have a partner in life, especially as we age. So we don't wanna deny our aging parent companionship and love later on, but we certainly wanna protect and preserve what maybe our predeceased parent helped our surviving parent build and acquire.

Kim Elliott: Yeah, and I would guess it's probably particularly important too from a healthcare perspective, right? What does your step-parent think that your mom might want versus what she shared with her children over the course of, 40, 50, 60 years, however long it may have been. How does that kind of come into play?

Candace Dellacona: That's where the healthcare proxy or the healthcare power of attorney comes in very handy. Because ambiguity breeds conflict. So having documents that

Kim Elliott: Put that on a T-shirt.

Candace Dellacona: I should, should we market that? Gray Monster and Sandwich Generation Survival Guide says.

But it's true, Kim, that, having these people actually have the requisite authority in a document so you know who is going to be making that decision. And I think that not having that conversation leaves so much to chance, and it will guarantee you conflict.

So making sure that your healthcare wishes are known. If your dad is giving that right to his new spouse that he's only been married to for six months, it's important that you know that.

Kim Elliott: Yeah. Yeah. That's really important. We have a few more questions. Can we go a bit longer?

Candace Dellacona: Yeah, let's do it.

Kim Elliott: Okay.

Minimal Plans Advance Directives
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Kim Elliott: We had someone write in who said, "My mom insists she doesn't need an estate plan because she doesn't have much. What do I do?"

Candace Dellacona: The author is, it might be a little bit correct, or her mom may be a little bit correct that you may not need the Cadillac of an estate plan, but you certainly need advance directives, Kim, which is, again, the healthcare documents and the powers of attorney, because if something happens before you die and Mom doesn't have capacity, who has the legal authority to help her? So there are people that don't own property that may just have a bank account. If they have a beneficiary named on a bank account, then upon your death, you're right, that bank account will pass to the daughter. But what happens if you get sick before you die and you need someone to help you make sure your rent is paid or sign your tax return? So while she might not need the Cadillac of estate plan, she definitely needs advance directives.

Kim Elliott: Good to know.

Nursing Home Bills Liability
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Kim Elliott: One reader wrote in, "Can I be held responsible for my dad's nursing home bills if I never signed anything? Or what do I do if he's asking me to sign something so he can receive care?"

Candace Dellacona: Yeah. This is always a really tricky position to be in. Oftentimes when a loved one is admitted into a nursing home and it's unclear from the nursing home's perspective who's gonna pay that bill, they often request somebody called a guarantor. Someone who will be on the hook for the bill in the event that Medicare, let's say, or the private health insurance does not cover that bill. So certainly it depends on what is signed upon your loved one's admission to the long-term care facility.

But let's say you don't sign as a guarantor. You've never signed a document. Mom or dad goes into a long-term care facility, but you're the power of attorney, and Mom or Dad have assets. You are their fiduciary. You have a duty to make sure that if bills are accrued, that they are paid. So it's really important to go through those bills and make sure that if you have access and that bill should be paid, that you pay it. Now, does that mean that they can go after you personally? Probably not. But if you don't pay a bill and you're the one who's appointed to be the fiduciary, it could be a breach of your fiduciary obligation.

Estate Debts and Creditor Order
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Kim Elliott: So on that topic, a couple people have written in around what happens to a parent's bills when they die? It's not like, the electricity immediately shuts off at their home and, the lawn guy stops coming or whatever it might be.

Candace Dellacona: Yeah. When people pass away and they have bills outstanding, the people that are owed the money are called creditors. And so often when someone passes away and there are bills outstanding, there are creditors waiting to be paid. So if an estate goes through the probate process, those creditors have the ability to appear and raise their hand and say, "Hey, this person owed us money based on the following things that we did for them before their death." And the executor has the obligation to review those claims and determine whether or not they're legitimate and determine whether or not they should be paid. Now, if an estate has $10,000 and the creditor is coming forward with a $20,000 bill, the executor doesn't have to go into his or her own pocket to pay that bill. You only have to pay what the estate actually has.

Kim Elliott: But you have to pay it first. Let's say it's a credit card, and the credit card's $20,000, the estate only has $10,000.

Candace Dellacona: It depends, because there are certain creditors, Kim, that can rank higher than a credit card company. So for example, the federal government, like the IRS, would automatically be entitled to be paid before a credit card company.

In every state, there is an order in which creditors are supposed to be paid. That's why it's really important that you get local counsel before you start paying a bill, because you don't wanna pay the wrong creditor out of order.

Kim Elliott: That's good to know.

Medicaid Clawbacks to Children
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Kim Elliott: I know there's some laws, and you and I talked about this, Candace a few weeks back, where states can ... and again, this is another internet rumor, where like states can come after the adult children if a parent skips out on, an assisted living bill or nursing home bill.

Is that ever enforced? Can you talk me through that a little bit?

Candace Dellacona: Yeah, so I doubt it's an assisted living bill necessarily, but it could be Medicaid. And so often Medicaid is the payer for an assisted living or for a nursing home. They're the ones that are making payment. So if a person applies for Medicaid and transfers money to their adult child in order to qualify for Medicaid, in a way that they maybe shouldn't have, then Medicaid could go after the person who received the money.

Kim Elliott: And do they?

Candace Dellacona: They do in certain states, absolutely. Absolutely, and certain states are more aggressive than others. It's really important, you do not mess with the federal government. You do not mess with the federal government. You make sure that if a creditor is Medicaid or the IRS, you need to get counsel and understand what your rights and your obligations are.

Kim Elliott: Yeah.

AI and Online Legal Forms
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Kim Elliott: The I guess robot in the room, if you will, we got a bunch of questions about AI.

Candace Dellacona: Oh gosh, yeah.

Kim Elliott: I think at this moment a lot of people are like, "Hey, resources are limited." And of course, there's been ChatGPT and Claude and all of these tools. Can I just, have one of them draft this POA and the will, and all these documents that you're talking about, and then just go to my bank and have them witness it? What's your guidance there?

Candace Dellacona: Look, AI is an amazing, remarkable tool because it gives you a place to start. It can provide you a lot of information. I always tell people, technology is not to be discarded in a way to say that it is not helpful. That is not true. However, in the same way when you develop symptoms of whatever ails you, most people are not typing it in to ChatGPT to figure out if they have cancer or Parkinson's. You're going to an expert. It's the place you start.

When it comes to drafting legal documents, I think it's really important for our listeners and Gray Monster readers to know that powers of attorney often are statutory, and what that means is New York State, for example, has a form that has to be followed. The font has to be a certain size. Certain warnings have to be included in the document. There are powers that are in the law that have to be included, and there is language that has to be included.

If you go onto Claude and say, "Draw me up a New York State power of attorney," there's no guarantee it'll be correct, and often you find out it's an incorrect form after the person no longer has capacity and can no longer sign the document. So the risk is so significant to allow it to chance that I don't think it's worth it.

Kim Elliott: What about some of the online tools? If you're just kinda looking for something quick, run-of-the-mill, is that recommended?

Candace Dellacona: I'm gonna go back and say the same thing. That there are lots of websites that purport to be tools for legal advice and legal documents, and sometimes they're good forms and sometimes they're not. And it's really hard to parse through the noise and figure out what's good and what's not so great.

I think that there is a misconception that all legal documents and all lawyers are prohibitively expensive, and that's just not true. Particularly if you're somebody who has limited resources, organizations like Legal Aid or JASA will provide a lot of those documents at either no cost or a very low cost. I will tell you, too, that union members often have legal plans through their welfare funds that will provide basic legal documents absolutely free. So I think it's really important that you explore those avenues if your resources are limited before you go online and try to use one of these online versions of the forms.

I've seen, really badly drawn up documents that have left clients in a bad spot. And you know what happens, Kim, is that if, for example, you sign a power of attorney and it's not the right form for your state or it's missing something that's really important, and Mom or Dad already has dementia and they're too far gone to sign another document, you have to petition the court for a guardian or a conservatorship. And what that means is you're telling the court, "I don't think that Mom or Dad has capacity anymore."

It's a court trial where you bring the person to court and you say, "I don't think you have capacity." It's a terrible, awful, undignified pro- Yeah. Anyone, Anyone.

So that is to be avoided. So just making sure that your basic documents are in good form is really foundational and it's worth a couple hundred dollars. And again, if you don't have a couple hundred dollars, then look at those free legal resources in your community.

Out of State Executors
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Kim Elliott: Yeah, so we had one reader reach out really about out of state. They're out of state, their siblings are out of state. Nobody lives in the same state as their mom and dad. Do they need to have an executor and a POA that's local to where their mom and dad lives?

Candace Dellacona: Look, it's always ideal to have somebody local and close. But that's just not the way a lot of families are. We live in a big country. We have a lot of square mileage here, and so often family members are across the country or they're a flight away. So nominating a daughter or a son who lives in Alabama when you live in Michigan is absolutely okay.

And I think, too, with technology these days and the ability to do things online, it's not as difficult as it once was. Likewise with healthcare proxy, as long as the doctor or the care team can get in touch with your proxy, even if they live out of the country, if the doctor can reach that person, that's still a good healthcare proxy if the person knows of what your wishes are. So geography alone shouldn't prevent you from appointing who you feel comfortable with and closest to.

Death Certificates and Digitizing
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Kim Elliott: Do you have any guidance on like the actual of life and death as far as like, "Hey, legally you should usually get this many copies of a death certificate because this is, how many you'll need"? What is your recommendation around that? Because it is, to your point, a legal experience taking, the end of someone's life and wrapping that up legally according to the federal government.

Candace Dellacona: Yeah. Death certificates are often the proof that most entities require to make sure that somebody's actually passed away. In my experience, many of the financial institutions want certified copies of death certificates. So I think it's really important to have, 10 or 12 to start out with to make sure that you have them on hand. Often your local department of vital statistics can provide you additional certified copies if you run out. But often you order them with the undertaker or the funeral home when the person passes away.

Kim Elliott: How much of the documentation that an attorney would pull together should be digitized? If, getting back to the whole out of state and, kind of everyone being dispersed will organizations accept a digital version or a scanned version of a document?

Candace Dellacona: I think generally the answer is yes, other than wills. I think wills are the one document that most states are holding onto where they want the original document. And the reason why is if you can't provide an original last will and testament to a court, many courts say that there's a presumption that the person revoked it. That they threw it away, that they wanted a different will, or that they didn't want that will any longer. But Kim, powers of attorney, healthcare documents, even trust instruments, having a photocopy is usually sufficient. I will say with one caveat, banks and financial institutions sometimes ask to what they say inspect the original power of attorney, meaning they just want to look at it and make sure it's legitimate.

So they will ask to inspect it, but they won't necessarily hold onto it. But, one of the great bits of advice I received from an NYPD officer years ago who was my client, he said that particularly in New York City, what's really helpful is to take a picture of a healthcare proxy so that you have it in your phone.

So if you have an aging parent, aging loved one, and you're on the go, and that aging loved one ends up in the hospital, it's really nice to have a copy of a healthcare proxy right in your

Kim Elliott: Smart.

Candace Dellacona: so that you don't have to run home and get a document, so you have a photo of it. So that could be really helpful, having digital copies. Yeah.

Trust Funding Basics
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Kim Elliott: And so you brought up trust in that. A digital copy of a trust is okay. We had one reader write in about their trust and says, "My dad has a trust, but everything is in his name. Is that okay?" And there's levels to trusts, right? Revocable, irrevocable. Can you break that down for us?

Candace Dellacona: Yeah, what it sounds like is that the writer is saying that Dad created a trust and he didn't retitle the assets in the trust, and that happens a lot, Kim.

So for everyone out there listening, a trust is really just like a vessel. It's a vase that you put flowers in. And it doesn't control anything until you actually put assets in it. So instead of a bank account being in the name of Kim, we need the bank account to be retitled to the name of Kim's trust.

That's how the trust controls the asset. So for that reader, what I would say is go back to the lawyer who helped Dad create the trust and talk to the lawyer about funding the trust. And to your question about different types of trusts, yes, there are lots of different types of trusts. There's revocable and there's irrevocable and there are subcategories in those trusts. And, depending on what your needs are will drive the decision whether or not revocable or irrevocable makes the most sense for your estate plan.

Kim Elliott: Okay.

When Parents Need More Care
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Kim Elliott: Last question, and I don't know if this is a legal question so much as I think someone was just looking for guidance understanding that they've got the documents in place, but mom's struggling to live independently. They don't flex the documents, but when do they advise perhaps leaving the home, moving into more supportive care? What is the adult child's legal really responsibility it sounds like, reading their email, to ensure their parent is kept safe and living in a home that's safe?

Candace Dellacona: This is always sort of a tricky situation that a lot of those of us in the sandwich generation find ourselves in, where you're seeing the cracks in the armor and you're worried about safety. You could be worried about your aging parent driving around town and perhaps not having the greatest vision anymore or space perception. It could be fall risks that you're worried about in the home. And I think in either of those circumstances, that's a really nice opportunity to bring in a geriatric care manager. And for those who don't know, a geriatric care manager is often a social worker or a nurse that specializes in understanding the types of care that a senior could benefit from.

They can determine if the house is safe or the living situation is safe. They can connect you with the right doctors. They can also help you have the conversation with the aging parent in a way that's really hard to do. We know a lot of great ones, Kim.

Kim Elliott: Yes. Yeah, absolutely.

Wrap Up and Subscribe
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Kim Elliott: Well, this has been a lot of fun. I think it's been very informative. I've learned a ton. Thanks for having me on, and thanks for letting me take over your podcast.

Candace Dellacona: Yeah, love the takeover. Thanks for joining us. And for the Sandwich Generation Survival Guide listeners, you must subscribe to Gray Monster. It is a free newsletter. It hits your inbox every week on Sundays. Kim goes out of her way to find these amazing resources for those of us dealing with the scary Gray Monster in our lives. Thanks again, Kim.

Kim Elliott: Yeah. Thank you.

Candace Dellacona: Hey, survivors. Be sure to follow and subscribe to the Sandwich Generation Survival Guide wherever you get your podcasts so you never miss an episode. We're back with new conversations on the first and third Tuesdays of every month. If you're finding value in the show, I'd be grateful if you left a five-star review and shared it with other survivors navigating this season of life known as the sandwich generation.

For resources and a full library of past episodes, visit sandwichgenerationlaw.com. Follow the conversation on Instagram, Facebook, and TikTok @sandwichgenerationpodcast. Until next time, take care of yourself while surviving and hopefully thriving in the sandwich generation.