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This file was generated by Descript 

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Speaker: Welcome to Real Estate is Taxing,
where we talk about all things real estate

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tax and break down complex concepts into
understandable, entertaining tax topics.

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My name is Natalie Kalady, I'm
your host, and I am so excited

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that you've decided to join me.

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Microphone (Shure MV7): Hello.

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Hello everyone.

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And welcome to today's episode.

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Today.

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I want to circle back to the short-term
rental loophole a little bit.

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But we are going to talk
about some of the guidance.

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And court cases related to this topic.

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So I'm a big fan of reading court cases.

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I love reading tax court cases.

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They just add a ton of context.

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They add a lot of understanding.

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And to me that is.

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Immensely important.

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Right?

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That's what really helps us understand.

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What is meant behind the law.

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And not just have it be an
obscure thought on paper.

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So all of that said.

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We are going to dive into a
handful of court cases today

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related to short-term rentals.

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Some of these are not court cases,
they're revenue procedures, or revenue

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reviews or guidance or things like that.

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But we'll differentiate
what we're talking about.

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But all of these relate
to short-term rentals.

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The thing that prompted this.

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So I have always had some court cases.

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I've had sort of a folder of these.

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And I referenced them in my
short-term rental classes.

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I've always had some cases, but
I had a feeling there was more.

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And not too long ago, someone
shared an article with me.

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That was written by a pretty prominent,
like real estate related tax person.

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And they said.

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That the short-term rental loophole.

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I was risky because the laws
that allowed it were outdated.

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Because they were written
and existed before Airbnb and

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short-term rentals really did.

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And they also said that,
unfortunately, we didn't really

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have any court guidance on this.

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And neither of those things are true.

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That's not how laws work.

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Laws don't just become obsolete without
there being some kind of change to them.

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Right.

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So there are some laws.

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That have been replaced with other laws
or they have been adopted over the years.

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But there are plenty of
laws that were written.

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In the forties and the fifties.

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That are still what we use today.

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So even if a law is from forever
ago, If it still applies to

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the specific circumstance.

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Then, if it applies to this
specific circumstance, so tax

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laws, don't just become outdated.

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And then the next statement.

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That we didn't have any court cases
related to short-term rentals.

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Also just not true.

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There's quite a few.

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So We are going to jump through some of
these court cases and revenue rulings.

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And guidance related
to short-term rentals.

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if you want to read through
the whole entire thing.

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I'll provide a link in the show notes.

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So.

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That being said the first.

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Case we have to look at today.

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It's from 1965.

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Now this case.

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Is actually from the us court of
appeals comes from the ninth circuit.

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And.

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Did Airbnb exist in 1965?

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No, it didn't.

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But do you guys think that renting of
property has existed for centuries?

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Yes.

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And do you think renting property
for various lengths of time

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has existed for centuries?

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Also, yes.

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So even though the like,
present most common.

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Experience of short-term
rental didn't exist in 1965.

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It's still existed as a, as a premise,
as something that could be clarified and.

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Defined by law.

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So this was actually not a tax court case.

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This was from the us court of appeals.

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So this was Dell, Dell?

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No, D E L N O.

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V Celebrita C E L E B R E Z E.

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And in this case, this was the first
case I could kind of find earliest.

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I could find.

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At the end of the day, in this
case, what ended up happening?

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This was a mixed use property
with some short term, some longer.

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But those shorter term, Units
were almost more for in-home care.

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Like they provided really
a little bit more to them.

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It was almost like supervise rentals.

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And so even though that was the
case, so some of these units

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were rented on shorter basis.

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And the taxpayer did.

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A fair amount of what we would really
now consider substantial services.

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So in this case, the taxpayer went in
a few times a month, like two to three

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times a month and cleaned and maintain the
kitchens to make sure they didn't get to.

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Like in too bad of shape.

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They would clean the windows quarterly.

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They had that professionally cleaned.

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And in addition to this,
the taxpayer would even do.

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Trash removal.

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And not just from.

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Like these shared areas,
which is incredibly common.

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That's not a substantial service.

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But the taxpayer would literally
go into the apartments.

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Remove their bag of trash,
taken out to the dumpster.

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In today's terms, like
kind of what we know today.

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If someone was coming in a few times a
month and cleaning for me and cleaning my

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windows and taking out my trash every day.

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Those are probably substantial
services that's above and beyond the

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standard of what you would receive.

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In a longterm rental.

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These are services that have
a substantial value to them.

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However, in this case in 1965.

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It was determined that in spite of that
happening, it wasn't on every unit,

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but it was on a fair amount of them.

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And it was like 15 units.

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In spite of all of these services.

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The court ruled that these were
essentially not substantial services.

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They decided this taxpayer's income
was not subject to self-employment tax.

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We only have self-employment tax
on rentals when they are providing

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those substantial services.

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And the court decided that
didn't come to that level.

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Even though it was a handful of services
that did have a fairly decent value.

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The big, final point.

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Of the court in this case.

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Was the idea that it
was close to impossible.

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To fully separate.

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The investment of someone's capital
into real estate with the requirement

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of an investment of their time.

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That.

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In most circumstances, if someone was
buying property to rent, That there was

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some time requirement kind of tied in with
conjunction to the money they put into it.

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It wasn't typically one or the other.

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Now I'm not super familiar
with the real estate market

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in 1965 or what was standard.

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My guess is there were less, less options
available for like property management.

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We obviously didn't have the
same kind of technical and

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digital tools that we have today.

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So my assumption is that it was
much more common for anyone who

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was a landlord at those times.

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To have to kind of put some more
time into the overall maintenance

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and management of their properties.

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So the court basically said that it's
really hard to separate those two things,

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your investment in real estate, with
the amount of time it takes to sort of

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operate your investment in real estate.

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So even though there was
multiple cleanings during the

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month external cleanings on
windows and trash removal daily.

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The court decided that that was still
not subject to self-employment tax.

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So that's kind of a big win.

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On our side of things, right.

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We do not want rentals on schedule
C paying self-employment tax.

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The next item of guidance that
came out was a revenue ruling.

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And this was revenue ruling, 72 dash 3 31.

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And this was actually an
example of a mobile home park.

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And in this court case, the
taxpayer provided what we would now

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consider very standard services.

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They would maintain the like city
utility lines into the property.

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They were maintaining the communal
like laundry area and bathrooms.

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Like if there was a
shared public bathroom.

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And they were also maintaining the road
that led into the community, like the

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public road, if it snowed, if it needed
to be repaved, any of those things.

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The property owner maintained.

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They didn't do anything to the
people's individual mobile homes.

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Just overall community maintenance.

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And in this revenue ruling in 1972.

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It was decided that those services.

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We're outside of the normal scope.

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Of what would be provided for
the rental of rooms or spaces?

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Only for occupancy.

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So this 1972 case.

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This revenue ruling.

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Decided that that income was indeed.

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Subject to self-employment tax.

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So that's a little kooky because.

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Most of those are pretty standard.

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But at the time it wasn't.

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So this is why looking back
at these guidance points is

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really important because you
can kind of see the progression.

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Of where things adapted and where
the courts and guidance shifted.

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So first, first case from court of
appeals, 1965, lots of services.

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No self-employment tax.

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1972 Riverland came out for a mobile
home park and said, yeah, self-employment

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tax, even though all they're doing
is maintaining the shared spaces.

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This then gets kind of contrasted.

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In 1983.

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So it's about 10 years later.

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We have revenue ruling, 83 dash 1 39.

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And in this example, We have
another mobile home park.

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And this rev ruling is incredibly
important because it ends up.

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Basically.

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Replacing or voiding reveling
seven two dash 3 3 1.

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It makes that obsolete.

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No longer something
that can be relied upon.

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It basically crossed it out, replace
it with a new train of thought.

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So in between these two revel rulings.

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1972, we have self-employment
tax for maintaining general

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areas of mobile home park.

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By 1983.

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We have a rev ruling that goes the
other direction and says, don't worry.

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We're not even looking at that
one from 10 years ago anymore.

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It's obsolete.

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In between these two.

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In 1978, there was a
mobile home park case.

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This was a tax court case.

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And this was Bobo V commissioner.

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And in this case, it was a lot
of the same things from that

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earlier reveling, they maintained.

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Utilities, they provided heat and light.

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They kept public areas clean.

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They collected trash from
like outside the properties.

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When people would put out their
trash cans, And in this court case.

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It was determined that those things
did not generate self-employment tax.

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So 1972 rev ruling says the up doing
all these kinds of communal area

00:10:55.598 --> 00:10:57.218
things create self-employment tax.

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Six years later, the tax
court says, no, it doesn't.

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That's not doing a substantial service.

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To the tenant to like,
make their stay better.

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It is not something provided for the
convenience and improvement of their

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actual occupancy of the location that has
a substantial value where like they're

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paying more rent for these services.

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They were like on any
property, maintaining.

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Like the communal spaces and the road
and making sure trash doesn't pile up.

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Those are just normal.

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That's just has to happen for any rental.

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So 1978 tax courts, like, Nope.

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That is not self-employment tax.

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We're not doing it.

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So then, like I said, by
1983, we have that RiverLink.

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Which agreed with it.

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It was a similar case.

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But in that rev ruling
eight three dash 1 39.

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This mobile home park did
all of those same services.

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The communal areas.

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Cleaning up trash,
maintaining utility lines.

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But.

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This mobile home park
also had extra facilities.

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So in this circumstance,
they also had a recall.

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Which had a card area and a pool room,
an auditorium, a theater with a stage.

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And they were all staffed by employees.

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And on top of that, it was noted that they
would host numerous recreational events.

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So in this case, This 1983 rev ruling.

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They decide that this is what is
subject to self-employment tax.

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This is obviously far above and
beyond those earlier two cases

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related to mobile home parks.

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It's not just maintaining somewhere
for you to park your home.

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They're providing extra spaces.

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They're providing people
to run those spaces.

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They are providing events.

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They are giving you all kinds of
extracurricular activities and people

00:12:43.748 --> 00:12:45.458
there to set it up and keep track of it.

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So that's the level.

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Where we have self-employment tax.

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So this reveling specifically made.

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That initial one revenue ruling 72, 3 31.

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Obsolete.

00:12:58.288 --> 00:13:00.178
What they basically determined.

00:13:00.598 --> 00:13:04.408
In this ruling, is that whenever we're
looking at a short-term property or

00:13:04.408 --> 00:13:05.908
any kind of rental property, really.

00:13:06.408 --> 00:13:09.618
But when you are analyzing this, there
kind of has to be a two-step approach.

00:13:09.618 --> 00:13:11.118
And that's what they took here.

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And that's what they
suggested pretty much.

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So step one.

00:13:15.108 --> 00:13:18.498
Is figuring out if there
are services provided.

00:13:19.068 --> 00:13:22.308
For the convenience of
the occupant, right.

00:13:22.308 --> 00:13:23.688
Are they providing something?

00:13:24.228 --> 00:13:28.578
That is directly related to their stay to
make it easier to make it better, or is

00:13:28.578 --> 00:13:30.318
it just sort of overall maintenance items?

00:13:30.828 --> 00:13:31.938
So that's the first step.

00:13:32.438 --> 00:13:34.898
Even after you identify those things.

00:13:35.438 --> 00:13:39.188
Because could it be argued that
picking up trash for someone

00:13:39.188 --> 00:13:40.328
is for their convenience.

00:13:40.718 --> 00:13:41.498
Absolutely.

00:13:42.278 --> 00:13:44.588
But it's also not uncommon.

00:13:44.618 --> 00:13:47.378
So first step is figuring
out if their services.

00:13:48.218 --> 00:13:49.418
The second step.

00:13:49.988 --> 00:13:51.698
Is then you need to figure out.

00:13:52.298 --> 00:13:55.448
Whether the value of
those services provided.

00:13:56.018 --> 00:14:01.448
Makes up a material portion of the
payments being collected for rent.

00:14:01.928 --> 00:14:03.308
From the occupants.

00:14:03.808 --> 00:14:07.648
So this was a super important revenue
ruling because it gives us this

00:14:07.648 --> 00:14:09.778
mindset and clearly states this.

00:14:10.738 --> 00:14:11.788
Two step approach.

00:14:12.448 --> 00:14:16.468
And I get asked this quite a bit
from taxpayers and tax professionals.

00:14:16.968 --> 00:14:20.478
Who will say, Natalie, we
have a short-term rental.

00:14:20.808 --> 00:14:25.368
We do provide this service, but we
don't do these other five services

00:14:25.368 --> 00:14:27.078
that are typically seen as substantial.

00:14:27.648 --> 00:14:30.948
Is it subject to self-employment tax
or from only doing this one thing?

00:14:31.668 --> 00:14:34.728
And like with a lot of things in
tax, the answer is, it depends.

00:14:35.358 --> 00:14:37.098
But this is the consideration.

00:14:37.578 --> 00:14:41.838
What we learned from this 1983
rev ruling this two step approach.

00:14:42.378 --> 00:14:47.868
So if a property is providing any kind
of services, You then have to look

00:14:47.868 --> 00:14:50.208
at, do they have a substantial value?

00:14:50.848 --> 00:14:51.988
Is the amount.

00:14:52.378 --> 00:14:56.638
Where the value of these services,
does that make up a material portion?

00:14:57.358 --> 00:14:58.258
Of the amount.

00:14:58.618 --> 00:15:00.268
That the occupant is paying in rent.

00:15:01.168 --> 00:15:05.668
If it doesn't, if these are things that
on their own are pretty insubstantial

00:15:05.898 --> 00:15:09.438
Then they're not as substantial service,
they're just sort of an incidental.

00:15:09.918 --> 00:15:11.268
So keep that in mind.

00:15:11.328 --> 00:15:15.138
Two part approach are there
services and if there are.

00:15:15.678 --> 00:15:17.688
What's the real value to them.

00:15:18.078 --> 00:15:19.368
If it's not a large amount.

00:15:20.118 --> 00:15:22.848
Then it's likely, still not
subject to self-employment tax.

00:15:22.848 --> 00:15:24.408
Microphone (Shure MV7)-1: by
this point, we're really sort of

00:15:24.408 --> 00:15:26.088
starting to set a standard, right?

00:15:26.088 --> 00:15:28.038
Like we are starting to prove.

00:15:28.548 --> 00:15:31.098
What they consider a substantial service.

00:15:31.098 --> 00:15:34.368
We are getting some good, clear examples
of the differences that are looking at,

00:15:34.968 --> 00:15:36.528
and we get to take this and move forward.

00:15:37.428 --> 00:15:39.408
So there are a handful of more cases.

00:15:40.338 --> 00:15:43.368
That relate to this and some of them.

00:15:43.758 --> 00:15:46.218
Actually came from a unique angle.

00:15:47.058 --> 00:15:49.548
Which there's a handful of court cases.

00:15:50.238 --> 00:15:51.558
That came into play.

00:15:52.248 --> 00:15:55.428
Because of taxpayers applying
for retirement benefits.

00:15:55.878 --> 00:15:58.578
So when you go to apply for
social security or like certain

00:15:58.578 --> 00:16:01.488
insurance benefits, you need to
have a certain amount of quarters

00:16:01.488 --> 00:16:03.948
that you paid in to the system.

00:16:04.488 --> 00:16:06.168
So there were several cases.

00:16:06.678 --> 00:16:11.028
We're taxpayers who owned real estate
were trying to argue that it did

00:16:11.028 --> 00:16:13.068
qualify for self-employment tax.

00:16:13.398 --> 00:16:18.648
They wanted to switch it over
to being schedule C non-passive

00:16:18.648 --> 00:16:20.058
and paying self-employment tax.

00:16:20.598 --> 00:16:23.088
Because they didn't
have enough time put in.

00:16:23.478 --> 00:16:27.648
To now qualify for the benefits that
they were looking for in retirement.

00:16:28.368 --> 00:16:33.018
So there's a handful of these cases,
but one of my favorite ones or the

00:16:33.018 --> 00:16:37.608
one that I think was kind of most
clear, we had this case in 1986.

00:16:38.118 --> 00:16:40.698
And this was another court of appeals.

00:16:40.788 --> 00:16:42.858
So this was a ninth circuit
court of appeals case.

00:16:43.398 --> 00:16:45.918
And this was a Holohan B heckler.

00:16:46.418 --> 00:16:46.868
So.

00:16:47.368 --> 00:16:48.538
In this example.

00:16:49.198 --> 00:16:51.358
This taxpayer had actually.

00:16:51.758 --> 00:16:54.788
Reported a piece of real estate
that they owned for years and years.

00:16:54.788 --> 00:16:56.468
This was a commercial office building.

00:16:57.188 --> 00:17:00.098
And they were leasing it to
an army recruiting office.

00:17:00.818 --> 00:17:02.498
Now part of their lease.

00:17:02.998 --> 00:17:04.558
Specifically required.

00:17:04.558 --> 00:17:05.638
And this wasn't from the taxpayer.

00:17:05.638 --> 00:17:08.728
This was from like the military
requirement for using this space.

00:17:09.448 --> 00:17:14.548
Required that the taxpayer
did clean the office and the

00:17:14.548 --> 00:17:16.198
bathroom of the office daily.

00:17:16.918 --> 00:17:21.328
They would sweep, mop and
buff the floors monthly.

00:17:21.928 --> 00:17:23.938
And they would wash
all of the windows and.

00:17:23.968 --> 00:17:24.568
And kind of the X.

00:17:24.568 --> 00:17:25.348
Exterior.

00:17:25.738 --> 00:17:27.058
Quarterly as well.

00:17:27.488 --> 00:17:29.408
So these were quite a few services.

00:17:29.408 --> 00:17:30.878
The taxpayer was providing.

00:17:31.358 --> 00:17:32.618
That were outside of the norm.

00:17:33.118 --> 00:17:35.038
But they hadn't been
reporting it that way.

00:17:35.518 --> 00:17:38.728
Historically, they did not report
this as a schedule C rental

00:17:38.728 --> 00:17:40.258
subject to self-employment tax.

00:17:40.738 --> 00:17:44.068
They were reporting it on
schedule E as a passive rental.

00:17:44.698 --> 00:17:48.148
And then when they went to apply for
benefits and found out they didn't

00:17:48.148 --> 00:17:51.328
have enough time paid in and they
kind of looked over the requirements.

00:17:52.198 --> 00:17:53.668
The taxpayer said, oh,
well, wait a minute.

00:17:54.358 --> 00:17:58.678
I was doing a lot of these things that
would be more of a substantial service.

00:17:58.678 --> 00:18:00.148
So I'm going to amend.

00:18:00.718 --> 00:18:02.338
Three years of tax returns.

00:18:02.728 --> 00:18:05.728
So the taxpayer went back and amended
three years of their returns to

00:18:05.728 --> 00:18:09.958
move their rental, to schedule C and
to pay self-employment tax on it.

00:18:10.468 --> 00:18:13.678
So that they would have enough
quarters paid in to qualify

00:18:13.678 --> 00:18:14.998
for these retirement benefits.

00:18:15.838 --> 00:18:17.938
And ultimately in this court of appeals.

00:18:18.568 --> 00:18:23.728
They landed on the decision
that, that didn't qualify.

00:18:24.358 --> 00:18:27.358
That the services that this
taxpayer was providing.

00:18:28.168 --> 00:18:31.168
Did not subject them
to self-employment tax.

00:18:31.948 --> 00:18:33.088
They said that these.

00:18:33.688 --> 00:18:37.228
These services that are to me
above and beyond the standard,

00:18:37.228 --> 00:18:40.528
but, you know, cleaning daily,
that's pretty above and beyond.

00:18:40.978 --> 00:18:42.628
Monthly cleaning the floors.

00:18:42.898 --> 00:18:44.218
That's pretty above and beyond.

00:18:44.718 --> 00:18:48.948
They ruled that it was merely
incidental to the effective

00:18:48.978 --> 00:18:50.628
operation of the building.

00:18:51.438 --> 00:18:55.158
And that it did not subject the
taxpayer to self-employment tax.

00:18:56.088 --> 00:18:59.718
They lumped it in the same category
as the removal of trash, the

00:18:59.748 --> 00:19:03.408
installing of like water coolers
and air conditioning filters.

00:19:04.038 --> 00:19:10.548
They almost set in my mind, a separate
precedent for commercial office space.

00:19:10.938 --> 00:19:13.668
They, what is considered standard.

00:19:14.298 --> 00:19:16.848
For maintaining an office space
where there's going to be multiple

00:19:16.848 --> 00:19:17.898
people in and out of there.

00:19:17.898 --> 00:19:21.198
It's not like one tenant,
typically one person who is just

00:19:21.198 --> 00:19:22.848
staying there and responsible.

00:19:23.658 --> 00:19:28.008
They were saying that this is part of
the standard operations of offices.

00:19:28.578 --> 00:19:32.148
So we've now had this established
pattern that for a mobile home park.

00:19:32.778 --> 00:19:36.378
Doing the general grounds,
keeping, maintaining the premises,

00:19:36.408 --> 00:19:38.028
maintaining those shared spaces.

00:19:38.598 --> 00:19:39.888
Not self-employment tax.

00:19:39.918 --> 00:19:41.358
That is standard operations.

00:19:42.018 --> 00:19:45.978
And now this court case kind of says that,
you know, in an office building, setting.

00:19:46.458 --> 00:19:49.548
These more frequent cleanings because
there's going to be potentially

00:19:49.548 --> 00:19:50.958
the public coming in there.

00:19:51.268 --> 00:19:53.638
It is going to be shared
by numerous employees.

00:19:53.638 --> 00:19:57.298
It's not just like a family saying
there that the person who owns the

00:19:57.298 --> 00:20:01.138
property, maintaining it a little more
for that sort of public use almost.

00:20:01.918 --> 00:20:04.108
Is standard is part of the industry.

00:20:04.828 --> 00:20:08.248
So it's kind of an interesting case
because that is what we would consider

00:20:08.248 --> 00:20:13.858
today to be substantial services, if
provided that way in relation to any

00:20:13.858 --> 00:20:15.928
kind of a vacation rental, right.

00:20:16.528 --> 00:20:21.238
So the comparison we typically
use now is looking at a hotel for

00:20:21.238 --> 00:20:22.678
what is a substantial service.

00:20:23.368 --> 00:20:25.468
And examples of what you
would get in a hotel that are

00:20:25.468 --> 00:20:27.238
substantial are going to be.

00:20:27.658 --> 00:20:31.948
Services during your stay that
have a value daily cleaning,

00:20:31.978 --> 00:20:34.108
fresh sheets for us linens.

00:20:34.468 --> 00:20:36.538
Cleaning and vacuuming day to day.

00:20:37.138 --> 00:20:39.028
All of those things we would consider.

00:20:39.538 --> 00:20:42.898
Items that could shift it over to
being subject to self-employment tax.

00:20:43.738 --> 00:20:46.318
But in this case, what we're
seeing is very similar.

00:20:46.648 --> 00:20:48.238
Frequency of services.

00:20:49.048 --> 00:20:51.178
But sort of a different
scope of what is done.

00:20:51.678 --> 00:20:55.758
Are considered normal with
the realm of office building.

00:20:56.238 --> 00:21:01.098
So kind of an interesting
counterpoint here that was 1986.

00:21:01.248 --> 00:21:03.318
We had another case
with a lot of services.

00:21:03.708 --> 00:21:05.088
No self-employment tax.

00:21:06.078 --> 00:21:07.878
There were a handful of other cases.

00:21:08.748 --> 00:21:13.028
That were somewhat related to this
where There was a case in 1967.

00:21:13.028 --> 00:21:14.228
So it kind of an older case.

00:21:14.258 --> 00:21:16.238
And in this one, they
were trying to decide.

00:21:16.898 --> 00:21:19.268
The property had been
incorrectly reported for a while.

00:21:19.268 --> 00:21:19.598
There.

00:21:19.958 --> 00:21:23.648
And essentially what happened
was it wasn't reported jointly.

00:21:24.638 --> 00:21:29.288
So then later on one of the taxpayer
or spouse, one of them had much

00:21:29.318 --> 00:21:33.578
more paid in than the other, even
though they shared and all of

00:21:33.578 --> 00:21:34.928
the management of the properties.

00:21:35.008 --> 00:21:36.508
They provided services together.

00:21:36.538 --> 00:21:38.338
This was schedule C property.

00:21:38.818 --> 00:21:39.358
But.

00:21:40.078 --> 00:21:43.738
The court in that one was like, Nope, you
don't have a clear proof of who did what?

00:21:43.738 --> 00:21:45.058
So we can't reallocate.

00:21:45.478 --> 00:21:48.808
So not super related, but just
something to be mindful of.

00:21:49.558 --> 00:21:51.838
Tracking and reporting correctly for who?

00:21:52.498 --> 00:21:57.058
Is actually doing the services on
a property, like whose rental is

00:21:57.058 --> 00:21:58.648
this or whose business is this?

00:21:59.128 --> 00:22:02.248
Because whether something is marked
for taxpayer or spouse or join.

00:22:02.848 --> 00:22:07.108
It's going to impact the amount
paid into your account, the taxpayer

00:22:07.108 --> 00:22:10.888
spouse to that specific person's
social security sort of their credit.

00:22:11.588 --> 00:22:13.448
There was another case in 87.

00:22:14.228 --> 00:22:15.098
That was Woodworth.

00:22:15.128 --> 00:22:17.348
And this was a us district court case.

00:22:17.888 --> 00:22:21.098
And this one was a little bit interesting
because this was a partnership.

00:22:21.578 --> 00:22:25.898
Where it was a passive rental, but
one of the partners was who did all

00:22:25.898 --> 00:22:27.398
of the maintenance on the property.

00:22:27.968 --> 00:22:29.228
And this isn't uncommon.

00:22:29.978 --> 00:22:33.698
So this taxpayer did all of the
repairs and handyman services.

00:22:33.728 --> 00:22:35.528
They did pretty much everything possible.

00:22:36.038 --> 00:22:39.788
And if it got to a point where something
was too complicated, they called in.

00:22:39.878 --> 00:22:41.138
You know, an outside contractor.

00:22:42.098 --> 00:22:44.078
The kind of unique piece to this.

00:22:45.068 --> 00:22:48.728
Was that, that taxpayer was also
being paid for their services.

00:22:49.328 --> 00:22:52.538
It wasn't like, it was just
their job within the partnership.

00:22:52.598 --> 00:22:55.088
They were operating it
as a separate business.

00:22:55.598 --> 00:22:59.528
So even though the partnership was their
only customer, they weren't doing handyman

00:22:59.528 --> 00:23:01.148
services for just the general public.

00:23:01.178 --> 00:23:02.558
They never advertise that.

00:23:02.948 --> 00:23:07.388
They only did work for this
building, this specific partnership

00:23:07.388 --> 00:23:10.598
with a commercial building in
it that they were part owner of.

00:23:11.288 --> 00:23:12.878
But they maintain it fully separately.

00:23:13.358 --> 00:23:15.458
They charged fees for it.

00:23:15.818 --> 00:23:18.308
They kept it tracked as a
separate business, separate set

00:23:18.308 --> 00:23:19.778
of books, separate bank account.

00:23:20.328 --> 00:23:21.528
All of these different things.

00:23:22.028 --> 00:23:24.818
And part of what almost
got him kind of caught up.

00:23:25.178 --> 00:23:26.948
Was even though he was being paid.

00:23:27.368 --> 00:23:28.298
For these services.

00:23:28.328 --> 00:23:31.838
So outside of the income and expense of
the partnership, he received a specific

00:23:31.838 --> 00:23:34.268
payment for the repairs and handyman work.

00:23:34.268 --> 00:23:34.898
He did.

00:23:35.528 --> 00:23:38.558
He almost never received
an actual check for it.

00:23:39.098 --> 00:23:42.308
He would just reinvest what he was
being paid into the partnership.

00:23:42.308 --> 00:23:44.348
So he would have more equity
in there and kind of, they.

00:23:44.858 --> 00:23:46.928
He would have more contributed
capital and more funds he

00:23:46.928 --> 00:23:48.158
had put into the partnership.

00:23:48.368 --> 00:23:51.788
So he never really received,
like in hand the payments.

00:23:52.328 --> 00:23:53.858
He did constructively.

00:23:54.218 --> 00:23:57.428
Like they use were payments
issued to him and then booked as a

00:23:57.428 --> 00:23:59.768
reinvestment back into the partnership.

00:24:00.638 --> 00:24:04.748
So at the end of the day, because of the
way it was structured, so specifically

00:24:04.748 --> 00:24:08.288
and run as a separate business and
he was receiving specific payments.

00:24:08.678 --> 00:24:13.358
They ultimately decided that it did
qualify for self-employment tax.

00:24:13.868 --> 00:24:16.388
So those constructive payments he
received, even though they never

00:24:16.388 --> 00:24:20.078
hit his bank account, he booked
them as income and reinvested it

00:24:20.078 --> 00:24:21.218
right back into the partnership.

00:24:21.608 --> 00:24:27.208
They were allowed to count that as
income and quarters that counted towards

00:24:27.208 --> 00:24:29.488
paying in for his social security credit.

00:24:30.088 --> 00:24:31.858
So that was kind of interesting.

00:24:32.278 --> 00:24:36.748
The other key point that the
court really reiterated with this.

00:24:37.738 --> 00:24:41.338
Was that it wasn't fair to just say
that these services were part of

00:24:41.338 --> 00:24:43.318
the partnership, income or expense.

00:24:43.858 --> 00:24:47.638
Because it wasn't something incurred
and it wasn't something where all of the

00:24:47.638 --> 00:24:49.228
partners were receiving payment for it.

00:24:49.918 --> 00:24:54.928
It's not like the entirety of everyone
in the partnership was affected by this.

00:24:55.588 --> 00:25:00.298
This extra work and the income from
it only related to the one taxpayer.

00:25:00.748 --> 00:25:04.408
So that was kind of a big sticking
point for them where they said

00:25:04.408 --> 00:25:06.208
this was really run separately.

00:25:06.628 --> 00:25:09.418
From the operations of the building.

00:25:10.348 --> 00:25:12.298
So something to be mindful of.

00:25:12.388 --> 00:25:14.638
I know that there's quite a
few taxpayers who they want

00:25:14.638 --> 00:25:16.048
to set up property management.

00:25:16.378 --> 00:25:18.298
But only manage their own properties.

00:25:18.868 --> 00:25:21.658
This is a good case to look
at for precedent for that.

00:25:22.378 --> 00:25:25.228
Because it walks you through some
of what they liked and didn't

00:25:25.228 --> 00:25:26.788
like about how this was set up.

00:25:27.268 --> 00:25:30.358
And it could help give you some more
guidance to make sure that you and

00:25:30.358 --> 00:25:31.978
your attorney and tax professional.

00:25:32.608 --> 00:25:36.808
Have your management company set up
in a way that it is valid and not

00:25:36.808 --> 00:25:38.338
just considered kind of intermixing.

00:25:38.698 --> 00:25:41.818
So that was the Woodworth case from 1987.

00:25:41.818 --> 00:25:42.478
That was a us doctor.

00:25:42.808 --> 00:25:44.068
District court case.

00:25:44.568 --> 00:25:46.638
We had another unique case.

00:25:46.968 --> 00:25:49.398
A little bit obscure, but same category.

00:25:49.588 --> 00:25:52.798
2013, this one was a Morehouse case.

00:25:53.128 --> 00:25:55.678
And this related to land rental.

00:25:56.158 --> 00:25:58.708
But what was interesting with this case?

00:25:59.248 --> 00:26:02.638
Was that he was part, the
taxpayer was part of a program.

00:26:03.148 --> 00:26:06.598
Part of a government program So this
program would pay you a certain amount.

00:26:07.108 --> 00:26:10.498
To maintain your land in a way to
encourage wildlife that was natural

00:26:10.498 --> 00:26:15.688
to the area or to help, you know,
replenish local wildlife populations

00:26:15.718 --> 00:26:19.288
or plants that needed to be replanted
that were kind of local to the area.

00:26:19.648 --> 00:26:26.068
So basically to bring specific amounts
of lands back to their original state.

00:26:26.828 --> 00:26:29.198
And in this case, the taxpayer.

00:26:29.198 --> 00:26:30.698
I was saying that.

00:26:31.118 --> 00:26:32.948
It was not subject to self-employment tax.

00:26:33.398 --> 00:26:36.128
They said I don't do
anything on the property.

00:26:36.308 --> 00:26:39.308
I have these hundreds,
maybe thousands of acres.

00:26:39.908 --> 00:26:42.638
And the government pays me to make
sure they have certain plants and

00:26:42.638 --> 00:26:45.578
that, you know, they're not overgrown
in this way and kept kind of according

00:26:45.578 --> 00:26:50.738
to these specifics and I pay a third
party to maintain that land for me.

00:26:50.948 --> 00:26:54.998
So all I'm doing is getting paid
for the use of my land and then

00:26:54.998 --> 00:26:56.108
someone else's maintaining it.

00:26:56.138 --> 00:26:57.458
I'm not providing a service.

00:26:57.998 --> 00:27:02.178
And in that case in 2013 the
court did decide that that was

00:27:02.178 --> 00:27:03.678
subject to self-employment tax.

00:27:04.098 --> 00:27:05.898
Because they were like,
this is above and beyond.

00:27:05.928 --> 00:27:09.108
Just renting someone, your land with no.

00:27:09.588 --> 00:27:12.618
Other stipulation or no other
use to it, no other anything.

00:27:13.278 --> 00:27:17.418
They had to do a fair amount of
work month to month to keep all of

00:27:17.418 --> 00:27:19.788
this acreage meeting the criteria.

00:27:20.298 --> 00:27:21.018
So.

00:27:21.738 --> 00:27:25.518
Again, in this case, they decided that
was subject to self-employment tax

00:27:25.518 --> 00:27:29.718
because it was so different from the
standard expectation of a land rental.

00:27:30.528 --> 00:27:33.588
Kind of interesting to look at
it next to the earlier case.

00:27:34.308 --> 00:27:37.788
Of the army recruiting office, where
it was part of their contract, that the

00:27:37.788 --> 00:27:41.838
taxpayer had to do these extra services,
specifically the daily cleaning, the

00:27:42.148 --> 00:27:46.258
quarterly cleaning of the windows,
the monthly floor cleaning and waxing.

00:27:46.648 --> 00:27:50.248
That was also per a specific
contract and they decided it was

00:27:50.248 --> 00:27:51.898
not subject to self-employment tax.

00:27:52.558 --> 00:27:55.648
Because those services, as
it related to normal office

00:27:55.648 --> 00:27:57.778
rental, Weren't that different.

00:27:58.348 --> 00:28:01.978
But in this case, the extra planting
and mowing and tilling and all of these

00:28:01.978 --> 00:28:06.088
things that were very specific with very
specific species and certain criteria.

00:28:06.538 --> 00:28:09.148
That was very different than
the standard land rental.

00:28:09.388 --> 00:28:11.158
So not all things are black and white.

00:28:11.188 --> 00:28:12.088
They're going to look at.

00:28:12.418 --> 00:28:14.428
What services the taxpayer's providing.

00:28:15.118 --> 00:28:16.198
If there are services.

00:28:16.768 --> 00:28:19.018
What they are, if they're substantial.

00:28:19.618 --> 00:28:22.018
And how they relate to that industry.

00:28:22.318 --> 00:28:23.818
That's the other thing
we're seeing, right?

00:28:23.818 --> 00:28:24.958
That the expectations.

00:28:25.348 --> 00:28:27.058
Related to a mobile home park.

00:28:27.598 --> 00:28:31.408
An office building or land rentals
are going to be very different.

00:28:32.278 --> 00:28:34.258
So those are some of the key cases.

00:28:34.598 --> 00:28:36.128
And then pretty recently.

00:28:37.028 --> 00:28:42.488
We did have a court case that came up
that related to short-term rentals.

00:28:43.028 --> 00:28:44.768
In somewhat of an unexpected way.

00:28:45.128 --> 00:28:47.588
This case was related to a yacht rental.

00:28:48.218 --> 00:28:50.288
But the big takeaway from this.

00:28:50.708 --> 00:28:52.718
And this was a Rogerson.

00:28:52.748 --> 00:28:54.958
V commissioner case this was in 2023.

00:28:55.018 --> 00:28:56.188
So this was very recent.

00:28:56.938 --> 00:29:00.388
And same kind of argument here
as with short-term rentals, where

00:29:00.388 --> 00:29:03.308
they were arguing, it was going to
stay passive or it was going to be

00:29:03.308 --> 00:29:05.108
non-passive based on the length of stay.

00:29:05.828 --> 00:29:08.828
And the key takeaway from
this most recent case.

00:29:10.248 --> 00:29:15.408
Was that they hadn't had any guest
stays by the end of that year.

00:29:16.068 --> 00:29:19.368
So the year when they put it in service
and it might've been available to rent,

00:29:19.368 --> 00:29:23.118
which does make it in service, but no
one had technically stayed in it yet.

00:29:23.868 --> 00:29:25.518
And so for the argument.

00:29:26.018 --> 00:29:28.388
Of a rental of real property.

00:29:28.418 --> 00:29:31.838
So like a boat with living
facilities on it could qualify.

00:29:32.678 --> 00:29:35.828
If the average guest stay is
seven days or less, that it

00:29:35.858 --> 00:29:37.418
can potentially be non-passive.

00:29:37.838 --> 00:29:39.878
That was the argument
made by the taxpayer.

00:29:40.328 --> 00:29:43.748
And the court said, but you
don't have any guests for us

00:29:43.748 --> 00:29:45.338
to average and amount of stay.

00:29:45.938 --> 00:29:49.268
We have no way to know if your
first guest is going to stay

00:29:49.268 --> 00:29:51.458
for a hundred days or two days.

00:29:52.118 --> 00:29:55.358
So this very recent 20, 23 case.

00:29:55.898 --> 00:30:00.188
Really reinforced what a lot of us have
been saying, which is, if you are going

00:30:00.188 --> 00:30:03.968
to put your short-term rental, In service
before your end, you're going to try

00:30:03.968 --> 00:30:05.558
to do the short-term rental loophole.

00:30:06.038 --> 00:30:11.018
Make sure you have at least two
different stays at fair market value.

00:30:11.348 --> 00:30:14.198
So that you can prove an
average and you can prove an

00:30:14.198 --> 00:30:16.178
average of seven days or less.

00:30:16.838 --> 00:30:20.528
If you've put it in service, but
don't have anyone stay in it yet.

00:30:20.888 --> 00:30:23.348
Then you cannot prove it is
non-passive for the year.

00:30:23.378 --> 00:30:26.618
Even if it's in service, you can start,
you know, depreciating it as soon as

00:30:26.618 --> 00:30:27.848
it's ready and available for rent.

00:30:27.878 --> 00:30:29.138
All of that still happens.

00:30:29.798 --> 00:30:32.708
But we can not meet the criteria
to prove it is non passive.

00:30:33.098 --> 00:30:37.178
And this very recent court case
kind of reaffirmed what a lot of us

00:30:37.178 --> 00:30:38.738
have been saying in the tax world.

00:30:39.238 --> 00:30:40.588
So that was a lot of information.

00:30:40.768 --> 00:30:41.878
Like I said, I am.

00:30:42.238 --> 00:30:43.438
I'm huge on court cases.

00:30:43.438 --> 00:30:46.918
And this was actually like my night,
Friday night, I was up till three in

00:30:46.918 --> 00:30:49.858
the morning because I would find one
case and then it would lead to another.

00:30:49.858 --> 00:30:53.188
Cause it would say, you know, this,
this court referenced this other case.

00:30:53.188 --> 00:30:53.788
Well, okay.

00:30:53.788 --> 00:30:55.048
Now I'm going to go read that case.

00:30:55.468 --> 00:30:57.838
So that was my wild, Friday
night was staying up late.

00:30:57.898 --> 00:30:59.968
Reading through pages
and pages of court cases.

00:31:00.448 --> 00:31:02.218
But I find it super interesting.

00:31:02.698 --> 00:31:06.448
To me, this is the in between the lines
that is really important to add context.

00:31:07.138 --> 00:31:09.418
Because there's so much of it depends.

00:31:09.718 --> 00:31:15.718
When it comes to tax scenarios and part
of the difference between a tax preparer.

00:31:16.198 --> 00:31:17.818
And a tax strategist or planner.

00:31:18.328 --> 00:31:22.528
Is the ability to look at things
like this and form a position.

00:31:23.308 --> 00:31:25.708
There's lots of things in tax
that are not black and white.

00:31:26.248 --> 00:31:29.398
Where you as the taxpayer or
your tax professional, who

00:31:29.428 --> 00:31:30.718
you pay to help with this?

00:31:31.138 --> 00:31:35.428
Need to say, we believe we can
do this based on a, B and C, or

00:31:35.428 --> 00:31:39.328
we believe we can't or didn't, or
shouldn't have because of AB and C.

00:31:40.058 --> 00:31:44.648
That's what makes someone a tax
planner versus just a tax prepare is

00:31:44.648 --> 00:31:46.148
kind of that deeper understanding.

00:31:46.628 --> 00:31:46.958
So.

00:31:47.648 --> 00:31:49.988
I hope you guys have
found this really helpful.

00:31:50.258 --> 00:31:53.288
And if you are someone who loves reading.

00:31:53.338 --> 00:31:54.478
Interesting court cases.

00:31:55.048 --> 00:31:56.188
As much as I do.

00:31:56.728 --> 00:32:00.718
I will go ahead and link to these
cases and these show notes and

00:32:00.718 --> 00:32:03.178
these rev rulings, and you guys
can check them out for yourselves.

00:32:03.518 --> 00:32:04.328
Read a little more.

00:32:04.688 --> 00:32:09.248
If you have any followup questions, feel
free to join us in the Facebook group.

00:32:09.608 --> 00:32:13.148
There is one for tax professionals
and one for real estate investors.

00:32:13.148 --> 00:32:15.128
I will link both below as well.

00:32:15.608 --> 00:32:19.658
And as always, if you guys have
liked this episode or found

00:32:19.658 --> 00:32:21.548
value, please share the show.

00:32:21.548 --> 00:32:22.148
Review it.

00:32:22.538 --> 00:32:25.118
Leave it a good rating,
whatever you'd like to do.

00:32:25.368 --> 00:32:27.108
And as always.

00:32:27.678 --> 00:32:31.908
I will talk to you guys next week and
I hope you have a fantastic weekend.