Converting A Residence To A Rental

I have a client who owns a very nice house. Too nice, in fact, at least for its neighborhood. My client used to have a contracting business, and he used his business talents and resources to improve his residence. He is now thinking of moving to another city, and it is almost assured he will lose money when he sells his house.

He is quite creative in thinking of ways to make that loss tax deductible.

The first thought is to convert it to a rental. One can deduct losses on the sale of a rental, right?

There are two significant issues with this plan. One has to do with the amount of loss one can deduct when the rental is underwater – that is, when it costs more than it is worth. The second has to do with whether there actually is rental activity.

We have previously talked about the second point, especially when one rents to family. Doing so is not fatal, but doing so on the cheap (not charging rent or enough rent) is.

Consider the following:

The Langstons purchased a residence (75^th Place) in 1997.

They lived there until 2005, when they moved to an apartment. They kept some of their possessions at 75^th Place until they could move them to storage.

Renovations to 75^th Place were completed in 2010.

In 2011 they received an unwanted telephone call from their insurance agent. Someone had to live at 75^th Place or the insurance would be terminated.

In July, 2011 Mr. Langston rented the property to a fraternity brother for $500 a month.

COMMENT: The market rent was between $2,500 and $2,800 a month, but the fraternity brother would be home about five days per month. Mr. Langston prorated the rent accordingly.

In 2013 they finally sold 75^th Place. They deducted a loss of over $400 grand.

QUESTION: Do you think they successfully converted the property to a rental?

Let’s consider a few factors.

·      What was their intent when they moved to an apartment?

If the intent was to renovate and sell, this would indicate an income-producing purpose. The problem is that the renovations went on forever.

·      They tried to rent the property

No, actually they did not. In fact, the Court thought that they rented the property only after the insurance company threatened to cut-off their insurance.

·      They actually rented the property

For much less than market value rent. The Court was not impressed by that.

·      They tried to sell the property

Eventually, after nearly a decade and after never marketing the property. They did not even seek an appraisal until a refinancing required them to do so.

The Court decided that they never converted the property to a rental. There was no deductible loss.

Zero surprise. I get the feeling that the taxpayers did whatever they wanted for however long, and near the end they wanted some tax leverage from the deal. It was a bit unfair to the tax practitioner, as some planning – any planning – might have helped.

Let’s go crazy with their planning. What can we do….? Let me think, let  me… I got it! How about actually renting the place before the insurance company is about to drop you? How about charging market rent – or at least close?  How about listing the house with a realtor? Shheeesssh.

I suspect my client is shrewder than the Langstons. He however cannot get past the second tax issue.

You see, when you have a personal asset (say your residence) which you convert to income-producing status (say a rental), you have to look at its basis and its fair market value when you convert.

Basis is a fancy word for what you paid to acquire or improve the asset. Say that my client has $1.5 million in his house.

Say he converts May 1^st, when the house is worth $1 million.

He now has a “dual basis” situation.

His basis for calculating gain is $1.5 million.

But his basis for calculating loss is $1 million.

You see what happened? He was hoping to use that $1.5 million to calculate any loss on sale. Folks, the IRS figured out this gimmick ages ago. That is how we wound up with the dual basis rule.

I suspect the Langstons had a similar situation, but they never got to first base. You see, their activity had to qualify first as a rental before the Court would have to consider the dual basis rule. The activity didn’t, so the Court didn’t.

Our case this time was Carlos and Pamela Langston, TC Memo 2019-19.

The IRS Tests Deductibility Of Business Interest

You may be aware that the new tax law changed the deductibility of your mortgage interest. It used to be that you could borrow and deduct the interest on up to a million-dollar mortgage. That amount has now been further reduced to $750,000, although there is a grandfather exception for loans existing when the law changed.

COMMENT: I have never lived in a part of the country where a million-dollar mortgage would be considered routine. There was a chance years ago to relocate the CTG family near San Francisco, which might have gotten me to that rarified level. I continue to be thankful I passed on the opportunity.

There is also business interest. Let’s say you have a general contracting business. This would be the interest incurred inside the business. Maybe you have a line of credit to smooth out cash flows, or maybe you buy equipment using a payment plan. The business itself is borrowing money.

Business interest has traditionally avoided most of the revenue-rigging shenanigans of the politicians, but business interest got caught this last time. There is now a limit on the percentage-of-income that a business can deduct, and that amount is scheduled to decline as the years go by. You might see the limit referred to as the “163(j)” limitation, which is the Code section that houses it. Fortunately, you do not have to worry about “163(j)” if your sales are under $25 million. If you are over that limit (BTW related companies have to be added together to test the limit), you probably are already using a tax pro.    

Then there is investment interest. In its simplest form, it is interest on money you borrowed to buy stock in that general contracting business. The distinction can be slight but significant: it is interest on monies borrowed to own (as opposed to operate) the business.

There is a limit on the deductibility of investment interest: the income paid you as a return on investment. If the business is a corporation, as an example, that would be dividends paid you. If you do not have dividends (or some other variation of investment income), you are not deducting any investment interest expense. It will carry-over to next year when you get to try again.

I am looking at a case involving an electrical engineer and his sole-proprietor software development company. He was kicking-it out of the park, so he borrowed money to purchase two vacant lots. He also bought two steel buildings, with the intent of locating the buildings on his vacant lots and establishing headquarters for his company.

The business lost a major customer. Employees fled. He sold the steel buildings for scrap.

But he kept paying interest on the loan to buy the lots.

He deducted the interest as business interest, meaning he deducted it in full.

Oh nay-nay, said the IRS. You have investment interest and – guess what – you have no investment income. No deduction for you!

OBSERVATION: The business was still limping along, and as a proprietorship all its numbers were reported on his individual tax return.

The IRS had one principal argument: the buildings were never moved; the headquarters was never established; the land never used for its intended purpose. The “business” of business interest never happened. What he had was either investment interest or personal interest.

Let’s look at the definition of investment interest:

163(d)(5)  Property held for investment.

For purposes of this subsection –

(A)  In general. The term "property held for investment" shall include-

(i)  any property which produces income of a type described in section 469(e)(1) , and

(ii)  any interest held by a taxpayer in an activity involving the conduct of a trade or business-

(I)  which is not a passive activity, and

(II)  with respect to which the taxpayer does not materially participate.

I say we immediately throw out 163(d)(5)(A)(ii), as the taxpayer is and has been working there. I say that he is materially participating in what is left of the software company.

That leaves 163(d)(5)(A)(i) and its reference to 469(e)(1):

     469(e)  Special rules for determining income or loss from a passive activity.

For purposes of this section -

(1)  Certain income not treated as income from passive activity.

In determining the income or loss from any activity-

(A)  In general. There shall not be taken into account-

(i)  any-

(I)  gross income from interest, dividends, annuities, or royalties not derived in the ordinary course of a trade or business,

(II)  expenses (other than interest) which are clearly and directly allocable to such gross income, and

(III)  interest expense properly allocable to such gross income, and

(ii)  gain or loss not derived in the ordinary course of a trade or business which is attributable to the disposition of property-

 (I)  producing income of a type described in clause (i) , or

(II)  held for investment.

I am not clear what the IRS is dredging here, other than a circular argument that the interest was not incurred in a trade or business and was therefore held for investment.

The Court said that was an argument too far.

The Court could accept that the properties were not “used” in the trade or business, but it also accepted that the properties happened (the Court used the term “allocable”) because of the trade or business.

The Court allowed the interest as a business deduction.

Our case this time was Pugh v Commissioner.

Oh Henry!

It is a classic tax case.

Let’s travel back to the 1950s.

Let us introduce Robert Lee Henry, both an attorney and a CPA.  He was a tax expert, but he did not restrict his practice solely to tax.

He was also an accomplished competitive horse rider. After he returned from military service, the Army discontinued its horse show team. In response, he organized the United States horse show civilian team.

He met the wealthy and influential, benefiting his practice considerably.

Then he had to give up riding. Heart issues, I believe.

But he was quite interested in continuing to meet the to-do’s and well-connected.

He bought a boat.

He traded it in for a bigger boat.

He bought a flag for the boat. It was red, white and blue and had the numbers “1040.”

People would ask. He would present his background as a tax expert. He was meeting and greeting.

His doctor told him to relax and take time off. Robert Lee called his son, and together they took the boat from New York to Florida. They then decided to spend the winter, as they were already there.

Robert Lee deducted 100% of the boat expenses.

QUESTION: Can Robert Lee deduct the expenses?

NERDY DETAIL: The tax law changed after this case was decided, so the decision today would be easier than it was back in the 1950s. Still, could he deduct the boat expenses in the 1950s?

The key issue was whether the boat expenses were “ordinary and necessary.” That standard is fundamental to tax law and has been around since the beginning. Just because a business activity pays for something does not mean that it is deductible. It has to strain through the “ordinary and necessary” colander.

In truth, this is not a difficult standard in most cases. It can however catch one in an oddball or perhaps (overly) aggressive situation.

Robert Lee was an accomplished rider, and he had developed a book of business because of his equestrian accomplishments. He monetized his equestrian contacts. He now saw an opportunity to meet the same crowd of folk by means of a boat.

Problem: Robert Lee did not use the boat to entertain or transport existing clients or prospective contacts.

And there is the hook. Had he used the boat to entertain, he could more easily show an immediate and proximate relationship between the boat, its expenses and his legal and accounting practice.

He instead had to argue that the boat was a promotional scheme, akin to advertising. It was not as concrete as saying that he schmoozed rich people in the Atlantic on his boat.

He had to run the “ordinary and necessary” gauntlet.

Let’s start.

He continued to have a sizeable equestrian clientele after he left competitive riding.

Good.

He was however unable to provide the Court a single example of a client who came to him because of the boat, at least until years later. Even then, there still wasn’t much in the way of fees.

Bad.

So what, argued Robert Lee. How is this different from buying a full-page ad in an upscale magazine?

Quite a bit, said the Court. You gave up riding for health reasons. There is no question that you derived tremendous personal enjoyment from riding. You have now substituted boating for riding. Enjoyment does not mean that there is no business deduction, but it does mean that the Court may look with a more skeptical eye. It would have been an easier decision for us if you had bought a full-page ad. There is no personal joy in advertising.

As a professional, I have to develop and cultivate many contacts – business, social, personal, political – retorted Robert Lee. One never knows who one will meet, and it takes money to meet money. That is my business reason.

Could not agree with you more, replied the Court. Problem is, that does not make every expenditure deductible. What you are doing is not ordinary. Let’s be frank, Robert Lee, the average attorney/CPA does not keep a yacht.

They would if they could, muttered Robert Lee.

Even if we agreed the expenses were “ordinary,” continued the Court, we have to address whether they are “necessary.” This test is heightened when expenses may have been incurred primarily for personal reasons. You did sail from New York to Florida, by the way. With your son. And you deducted 100% of it.

I am meeting rich people, countered Robert Lee.

Perhaps, answered the Court, but there must be a proximate relationship between the expense and the activity. What you are talking about is remote and incidental. It is difficult to clear the “necessary” hurdle with your “someday I’ll” argument.

Robert Lee shot back: my point should be self-evident to any professional person.

COMMENT: Folks, do not say this when you are trying to persuade a Court.

The Court decided that Robert Lee could not prove either “ordinary” or “necessary.”

The conclusion that the expenditures here involved were primarily related to petitioner’s pleasure and only incidentally related to his business seems inescapable.”

The Court denied his boat deductions.

Our case this time for the home-gamers and riders was Henry v Commissioner.

How To Lose All Of Your Auto Deduction

I am not a fan of dumb.

And I am reading big dumb.

The IRS wanted over $22 thousand in taxes and $4,000 in penalties. There were several issues, but there was one that racked up the money.

What do you need if you want to claim auto expenses on your tax return?

Answer: some kind of record, like a log.

There is a reason for this. It is not random, chaotic or unfathomable.

The reason has two parts:

(1)  There was a very famous case decided in the 1930s concerning George Cohan. George was a playwright, a composer, a singer, actor, dancer and producer. He was very famous. He was also a terrible record keeper. Given his day job, he spent a ton of money schmoozing people. He deducted some of those expenses on his tax return, as he had to wine and dine to maintain his recognition, connections and earning power. Problem was: he kept lousy records. One had to – essentially – take his word for the expenses.

The Court, knowing who he was, thought it believable that he had incurred significant entertainment expenses. The Court simply estimated what they were and allowed him a deduction.

Ever since, that guesstimate has been referred to in taxation as the “Cohan rule.”

Problem was: everything can be abused. What started out as common sense and mitigation for George Cohan became a loophole for many others.

(2)  Congress got a bit miffed about this, especially when it came to travel, transportation and entertainment expenses. These expenses can be “soft” to begin with, and the Cohan rule made them gelatinous. Congress eventually said “enough” and passed Code Section 274(d), which overrides the Cohan rule for this category of expenses.

BTW, “transportation” is just a fancy tax-word for mileage.

The tax-tao now is: no records = no mileage deduction. Forget any Cohan rule.

Now, you do not need to record every jot and tittle as soon as you get in the car. Records can include your Outlook calendar, for example. You could extend the appointment by mileage from MapQuest and (probably) have the IRS consider it adequate. The point is that you created some record, at or near the time you racked up the mileage, and that record can be reasonably translated into support for your deduction.

Enter Gary Roy.

He was a consultant in Los Angeles. He worked out of his home and drove all over the place for business. He must have made a couple of bucks, as he purchased an Aston Martin Vantage.

This is not a car you see every day. Chances are the last time you saw an Aston Martin was in a James Bond movie.

You know he deducted that car on his tax return.

There are multiple issues in the case, but the one we want to talk about is his car. Roy appeared before the Court and straight-facedly claimed that he kept a mileage record for the Aston. He presented a sheet of paper showing mileage at the beginning of the year and mileage at the end of the year. He helpfully added the description “business use” so the Court would know what they were looking at.

As far as he was concerned, this was all the record-keeping he needed, as the car was 100% business use.

I want to be sympathetic, I really do. I suppose it is possible that he did not understand the rules, but I read in the decision that he used a tax preparer. 

COMMENT: To whom he paid $250. Given that there were complexities in his tax return – the business and a gazillion-dollar car, for goodness’ sake – he really, really should have upgraded on his tax preparer selection.

Roy had no chance. That stretch of tax highway has a million miles on it, and he missed the pavement completely.

Without the Cohan rule, the Court was not going to spot him anything. He just got a big zero. That is what Section 274(d) says. 

And is what Congress wanted back when.

Worst case scenario for Mr. Roy.

Difference Between An Advance And A Loan

Do you remember when the Washington Redskins and the Miami Dolphins went to the Super Bowl? It was 1983, and I was living in Florida at the time. I am pretty sure I was rooting for the Florida team. The Redskins had a hard-charging fullback named John Riggins. His nickname was “Diesel” and he scored a touchdown on a forty-something yard run. Blocking for him was (among others) George Starke, an offensive tackle. The Washington offensive linemen, the ones who block for the quarterback and running back, were known as The Hogs.

George Starke is second from the left.

George was very much on the backside of his career at that point. He shortly thereafter left football and opened a car dealership in Maryland. He couldn’t help but notice that the dealership had difficulty recruiting service technicians. He helped establish a technical school to educate and train technicians. He also hoped that - by providing a realistic hope for a better life – the school would also help with the poverty and violence in the area.

He eventually sold the dealership and cofounded the Excel Institute, a nonprofit program that provided a two-year reading, writing, arithmetic and technical skills curriculum. The program was free of charge, but one had to commit.

Starke received a salary and housing allowance, as well as a credit card. He would charge business and personal expenses on the card. The personal charges were segregated on the books and records. George discontinued any personal charges in 2006, and from 2007 onward the only activity relating to the credit card was a payroll deduction to repay the balance.

There was a change in the Board, and Starke did not like the new direction of things. He stopped fundraising. He left the Excel Institute altogether in 2010.

Excel put the remaining balance due from George of $83,698 on a Form 1099, sent a copy to George, a second to the IRS and figured that was that.

George did not include the $83 grand on his individual tax return, however.

The IRS noticed and insisted that George do so. George said no.

And off to Tax Court they went.

Before proceeding, tell me: do you think George has a prayer?

As you know, forgiveness of a loan triggers income. The tax issue is whether these monies were ever a loan.

Your first thought is: of course they were! Heck, he was paying it back, wasn’t he?

Let’s walk through this.

Just because someone gives you money does not mean that there exists a loan. A loan implies that both sides anticipate the monies will be repaid. It would also be swell if there were some attention to the basic formalities, like perhaps a loan agreement and repayment terms.

And – just to dream – maybe interest could be charged on the whole affair.

There was no loan agreement. Excel itself gave mixed messages to the Court on whether it thought the monies were a loan. George told the Court that he never had any intention of paying back the money, and that he thought the payroll deductions were for health insurance or something like that.

If not a loan, then what were the monies to George?

They were advances, akin to nonrecoverable draws.

Advances are more easily understood in a draw-against-commission environment. Draws are intended to provide some predictable cash flow to the salesperson. Say that a salesperson receives commissions, and against the commissions is a $5,000 monthly draw. There are two types of draws - recoverable and nonrecoverable. A nonrecoverable draw does not have to be paid back should a saleperson fail to meet quota. A recoverable draw does have to be paid back. Granted, a salesperson who fails on a continuous basis to meet quota would soon be unemployed, but that is a different conversation.  For our purposes, the key is that a nonrecoverable draw represents income upon receipt.

Back to our courtroom drama.

The IRS pulled his 2010 tax year.

George received no advances in the 2010 tax year.

George last received advances in 2006.

There was nothing to tax in 2010 because George received no monies in 2010.

The IRS should have pursued his 2006 tax year. They did not, nor could they under the statute of limitations.

The Court dismissed the case. George won. The IRS got embarrassed.

I am curious why the IRS even bothered. The only thing I can figure is that they were hoping for a miracle play. Maybe like John Riggins running that football for a touchdown in Super Bowl XVII with George Starke blocking for him.

Deducting Something, On Some Lake, Somewhere

Someone asked me during the busy season how I came up with the topics for this tax blog. 

It is whatever catches the eye of a somewhat-ADD 30-year tax CPA.  We are a bit of a garage tax blog, I guess.

What caught my eye this week was another case concerning rental property. It gives us a chance to talk about the “vacation home” rules. If you have a second home, odds are good that you and your tax preparer have talked about these rules.

Let’s say that a person – let’s call him Steve – buys a second home. It is in Tennessee. Steve likes Tennessee.

There are three things that Steve can do with his home in Tennessee:

(1) It can be a true second home. Steve, Mrs. Steve and Steve-descendants use it whenever they can. No non-Steves use the home.

(2)  It can be rented. Steve never uses it, as it is being rented to non-Steves.

(3)  Steve uses it some and rents it some.

It is (3) that drags us into the vacation home rules.

Let’s recall what the tax difference is between owning a house as a primary residence and owning it as a rental:

(1) Primary residence – you can deduct…

a.     Mortgage interest

b.     Real estate taxes

(2) Rental – you can deduct…

a.     Mortgage interest

b.     Real estate taxes

c.      Operating costs, such as utilities and insurance

d.     Maintenance costs, such as mowing in the summer and snow removal in the winter

e.     Depreciation

As you can see, there is a wider range of potential tax deductions if only we can qualify Tennessee as a rental.

Congress and the IRS know this. That is how we got the vacation home rules to begin with. You cannot rent out the place one week out of year, use it personally the rest of the time and deduct everything that is not tied down.

Our Code section is 280A and it is a math quiz:

(1) Did you rent the place for less than 15 days during the year?

(2) If no …

a.     Did you use it personally less than 10% of the days it was rented out?

Let’s go through it.

 

(1) If you rent the place for two weeks or less, the rental income is not taxable. Mortgage interest and real estate taxes are deductible the same as a residence.

COMMENT: Makes no sense, right? The IRS is actually letting you NOT REPORT income? How did that get in there? I bet it has something to do with Augusta and the Masters. It helps to know people who know people. 

(2) You rent it out more than two weeks and use it more than 10% of the rental days.

Congratulations, you have a second home. You also have rental income. You have to report the rental income, but the IRS is kind enough to allow you to take rental deductions UP TO A POINT. You cannot claim so many deductions that you reach the point of a tax loss. You must stop at zero

The deductions get allocated between the personal use days and the rental use days. It’s only fair.

Since it is a second home, you get to deduct whatever interest and taxes were not allocated to the rental as personal mortgage interest and personal real estate taxes.

(3) You rent it out more than two weeks and use it less than 10% of the rental days.

You still have to allocate the expenses as we discussed in (2), but the IRS now allows you to claim a rental loss. Why? Because at less than 10% personal use the IRS does NOT consider this to be your second home. The IRS considers it a rental.

There is a downside, though. You know that mortgage interest allocated to the personal use? It is not deductible anymore. Why? Because the only thing that made it deductible before was that it was attached to your second home.  As we said, under scenario (3) the IRS considers this to be a rental, meaning it is not your second home.

You do get to deduct the real estate taxes allocated to the personal use.  Taxes have a different tax treatment.

There are some special rules on counting days. For example, days spent repairing or maintaining the property do not count, either as personal use or as rental. You might want to document these days well, though.

What if Steve wants to allow Steve-descendants to use the place?

Most of the time this will not work. The reason is that Steve-descendants are considered to be Steve, and that means personal use days.

But there is small exception…

Steve-descendants will not be considered to be Steve if:

·     They pay fair market rent, and

·     They use the place as their principal residence

It is the second requirement that causes the problem. Put the house in Hilton Head or Key West and odds are that no one is using the place as a principal residence.

However, put a Steve-descendant into medical school in Tennessee and you may have the beginnings of a tax plan.

Our case this week is Cheryl Savello v Commissioner. She had more than one thing going, but our interest is whether she got to treat a Nevada property where her daughters stayed as rental property.

Her daughters used the place as their principal residence.

The Court agreed that the rent appeared to be market value, citing offers to rent from third parties.

But the Court decided that there was no rental. The daughters’ use was attributable to their mother.

What happened?

Her daughters didn’t pay the rent.