Tax Breaks On Selling Your Home, Vacation, Or Investment Property

With a personal residence, investment real estate, or other investment property, consider taxes before you sign. Your gain will often be long term capital gain, meaning a federal tax rate of 15 to 20%, depending on your income. Depending on your income, you may have to add another 3.8% in federal taxes. That’s the net investment income tax added by Obamacare. President Trump said he would repeal it, but so far that hasn’t happened.


That means up to 23.8% in federal tax, which is better than 39.6% on ordinary income. Add your state taxes too. But aren’t there breaks to eliminate or defer the taxes? First, you need to distinguish between personal use property, such as your principal residence, and investment or business property. If you sell your principal residence and have a gain, it’s taxable. However, if you have lived there as your primary residence for two years out of the last five, you can shield up to $500,000 of gain if you are married and file jointly. The exclusion is $250,000 if you file separately or are single.

Many people ask if there is a rollover rule allowing you to pour the gain from selling one residence into a new and bigger house. However, that “trading up” rule was repealed years ago. Still, the up to $500,000 exclusion can be used over and over, essentially every two years. You probably don’t want to move that often, but if you do, Uncle Sam can help subsidize it.

If you sell business or investment property, you can’t use the $500,000 exclusion. But you may be able to swap for other business or investment property tax-free. Section 1031 of the tax code allows you to exchange properties and roll over your gain into the property you receive in the swap. You can do it again and again. Despite a profit on each trade, you avoid tax until you cash out. Then, you’ll hopefully only pay one tax, a capital gain.

You can swap a ranch for an office building, a strip mall for a rental condo. Personal property also qualifies, so you can swap paintings, cars or machinery. However, it isn’t clear if swaps of cryptocurrency will qualify. In some swaps, there is depreciation recapture, and debts can sometimes trigger gain too.

A simultaneous one-for-one swap can be hard to arrange. For that reason, the vast majority of exchanges are delayed, three party, or Starker exchanges (named for the case that allows them). A middleman holds the cash after you “sell” your property. The middleman will use the cash to buy the replacement property for you. This three-party exchange is treated as a swap for tax purposes. There are several time limits to observe, so be careful about the details. That’s especially true if there is mortgage debt involved on either side of the deal. A reduction in total debt can be treated like cash, and that usually means tax.

Can’t you use 1031 to swap primary residences? No, 1031 is for investment or business property. But what about a vacation home or beach house? You might consider swapping one vacation home for another under 1031. You can turn a vacation home into rental property so you can do a 1031 exchange. Stop using your beach house, rent it out for a year (there’s no bright line, but that’s probably long enough), and then swap for other investment real estate. Some people try this with their primary residence too.

But what if you merely try to rent it but never have tenants? Timing, intent, and records will be important. However, merely trying to rent it for six months is probably not good enough. If you plan to use the newly acquired property as a vacation home or even as your primary residence, consider waiting. The IRS has said that it usually won’t challenge a 1031 exchange based on the investment nature of your new property as long as you actually rent the dwelling at a fair rental for 14 days or more, and if your own personal use of the dwelling does not exceed the greater of 14 days or 10% of the number of days during the 12 month period the dwelling is rented at fair value.

If you swap one vacation home or investment property for another, and then make it your primary residence, be extra careful. If you acquire property in an exchange and later attempt to sell it as your principal residence (to claim the $500,000 exclusion), beware. The exclusion does not apply during the five-year period beginning with the date you received the property in the 1031 exchange. Remember, trying to (legitimately) minimize your tax bill is as American as apple pie. Just make sure you dig into the rules carefully. I’ve simplified some of the details here. You don’t want to end up paying more taxes, penalties and interest later.

via The Tax Lawyer


Tax Evader Who Fled U.S. Gets 7 Years In Prison

A Grand Junction, Colorado man has been sentenced to 88 months in prison for tax evasion and failing to file personal and corporate income tax returns. Timothy Stubbs, 52, was convicted in September 2015 of tax evasion, willful failure to file an individual income tax return, and willful failure to file a corporate income tax return following a jury trial in Denver, Colorado. According to the evidence presented at trial, Stubbs owned National Rebate Fund Inc. in Grand Junction. Despite earning more than $7 million between 2005 and 2007, Stubbs did not file corporate income tax returns. Stubbs also earned more than $2 million in income taxable to him personally during those same years and did not file individual tax returns.


According to the evidence at trial, Stubbs had not filed a personal tax return since 1992, and had not paid individual income taxes since 1993. To conceal his income, Stubbs paid more than $700,000 in personal expenses from the business bank accounts and acquired more than $370,000 in gold and silver in 2007. The evidence also showed that during those three years Stubbs purchased real estate in Grand Junction and Crested Butte, Colorado, and two condos in Kailua-Kona, Hawaii, which cost in total more than $2.9 million dollars.

In December 2015, two weeks prior to his scheduled sentencing hearing, Stubbs removed his electronic GPS monitoring ankle bracelet and fled to Costa Rica, where he had been living in 2014, prior to being arrested for the indictment. According to documents filed with the court, Stubbs lied to immigration officials in Costa Rica in an attempt to renew his residency in Costa Rica, and to stay there permanently in an effort to avoid punishment in this case. In April 2017, Costa Rica deported Stubbs. He has been held in custody pending sentencing since that time and was remanded.

In addition to the term of prison imposed, U.S. District Court Judge Christine M. Arguello ordered Simard to serve three years of supervised release and to pay $639,114 in restitution to the IRS and a fine of $50,000. Stubbs had a long history of failing to file tax returns and to pay taxes. But he also manipulated his affairs to evade taxes and get around the IRS. Evasive and obstructionist behavior designed to avoid paying the IRS does not sit well with the agency, or with prosecutors.

Time and again, this issue comes up in criminal tax cases. Sometimes, that is even what can transform a regular civil IRS audit into a criminal tax case. Some taxpayers in a civil audit seem to think they can outsmart the IRS, or cleverly manipulate the government to come out ahead. Where the government sees this kind of behavior, they may want to crack down, harshly.

via The Tax Lawyer

Lessons From Dentist’s Tax Evasion: Cover-up Is Worse Than Crime

No one wants to be accused of tax evasion. And most people who end up in the situation probably did not think a criminal prosecution, much less a criminal conviction, was a serious or even a remote possibility. Recently, a Tennessee dentist named Andrea M. Henry pleaded guilty to tax evasion. Dr. Henry, 45, owned The Henry Polk Dental Group D.P.C. and The Smile Spa LLC. These dental practices were located in Cordova, Tennessee. Dr. Henry filed personal income tax returns for 2005, 2006, 2008 and 2010 to 2013, but did not pay $113,781 in income and self-employment taxes due to the IRS.


Dr. Henry also failed to pay over the employment taxes withheld from her employees’ paychecks for numerous quarters between 2006 and 2015. Given this failure to pay employment taxes, the IRS assessed over $160,000 in trust fund recovery penalties against Dr. Henry, making her personally liable for the unpaid employment taxes. Up to now, these were serious tax problems, but here is where things truly went off the rails. Instead of paying the taxes owed, Dr. Henry spent hundreds of thousands of dollars on personal expenses, including private school tuition, expensive housing and luxury cars. 

And that wasn’t all. After the IRS assessed penalties against her, Dr. Henry stopped using her personal bank accounts. Instead, she began using business accounts to pay for her personal expenses. In early 2011, prior to her home being foreclosed on, Dr. Henry transferred $130,000 to a nominee buyer, and entered into a sham lease arrangement with the nominee to create a false explanation as to the source of the funds in the nominee’s bank account. She even caused the nominee to repurchase the home for her. Dr. Henry later used that same nominee and other nominees to purchase and lease exotic cars, including a Dodge Viper and a Porsche Panamera.

Dr. Henry admitted to causing a tax loss of $528,882.07. Sentencing is scheduled for Jan. 12, 2018, before U.S. District Court Judge John T. Fowlkes Jr. These are serious charges, and Dr. Henry’s guilty plea means that only sentencing remains. Dr. Henry faces a statutory maximum sentence of five years in prison, a period of supervised release, restitution and monetary penalties. There are numerous lessons here. One is certainly that the IRS takes payroll taxes seriously. Although most payroll tax cases do not turn criminal, the IRS views using tax money withheld from employees as stealing from the U.S. Treasury. 

Being an officer or director usually means the IRS can pursue you personally for payroll taxes if the company fails to pay. When a tax shortfall occurs, the IRS can make personal assessments against all responsible persons with ownership in or signature authority over the company. The IRS can assess a Trust Fund Recovery Assessment against every responsible person under Section 6672(a). You can be liable even if have no knowledge the IRS is not being paid. The penalty can be assessed against multiple responsible persons, allowing IRS to pursue them all to see who coughs up the money first.

Another lesson relates to evasive and obstructionist behavior during an IRS audit, or similar behavior designed to avoid paying the IRS. Arguably, this is the bigger lesson of the case. It is surprising how consistently this theme arises in criminal tax cases. Time and again, taxpayers in a civil audit seem to think they can outsmart the IRS or cleverly manipulate the government to come out ahead. And understandably, where the government sees this kind of behavior, they may want to crack down, harshly.
This doesn’t mean that one has to agree with everything the IRS says in an audit. Yet, there is an established way of proceeding, and an above-board way to communicate with the IRS. And deception and obstruction are not the way. With a potential prison term of up to five years in this case, that is a painful lesson.

via The Tax Lawyer

Forest Whitaker Loses Tax Case, Provides IRS Handling Tips

No one wants to owe the IRS, or to have to ask the powerful tax collection agency for extra time to make payments. But it happens, even to wealthy and famous people. In Forest Whitaker v. Commissioner, No. 16-73450 (9th Cir. 2017), the Ninth Circuit Court of Appeals has dealt actor and director Forest Whitaker a blow about his own taxes. The case says the IRS did not abuse its discretion in rejecting Whitaker’s request for installment payments. The IRS instead demanded full payment, enforcing collection. The decision in favor of the IRS and against the actor and his wife should  hardly be a surprise. Yet installment payments are often quite possible with the IRS. So why did Whitaker lose?

NEW YORK, NY – SEPTEMBER 18: Forest Whitaker, UNESCO Special Envoy for Peace, speaks at The 2017 Concordia Annual Summit at Grand Hyatt New York on September 18, 2017 in New York City. (Photo by Riccardo Savi/Getty Images for Concordia Summit)

As with so many tax cases, the root of the problem goes back to some seemingly simple rules. Mr. Whitaker or his representatives failed to produce credible evidence to the IRS that they could or would pay. Yes, that is fundamental. Although Whitaker had previously had tax issues, this dispute started with his company, Salako, Inc., which paid him wages in 2013 and 2014. Whitaker’s joint income tax return for 2013 with spouse Keisha reported adjusted gross income of $1,491,974, and tax liability of $426,812. But his wage withholding only sent in $10,579 for taxes for the whole year! To that, he added estimated tax payments of only $4,500.

So on December 1, 2014, the IRS assessed the taxes of $426,812. This was not an audit. This was the amount Whitaker’s own 2013 tax return admitted that he owed. In early 2015, the IRS sent notices of intent to levy. Whitaker’s representative requested a Collection Due Process hearing, and an installment agreement calling for monthly payments. Citing a down movie trend and a need to project an extravagant lifestyle, Whitaker’s representative said the actor could not pay, but would pay monthly.

The IRS made clear that financials had to be filled out, that Whitaker’s 2014 return had to be filed, and that estimated taxes were also due. Whitaker and his representative failed to comply, but asked for an extension of time. The IRS checked on Whitaker’s 2014 wages, and found that Whitaker had 2014 wages of $1,865,077, but tax withholding of only $2,267. To the IRS, matters seemed to be getting worse, not better. The IRS said there could be no installment deal without better tax withholding.

Now, Whitaker wanted to make installment payments for his 2013 and 2014 IRS liabilities of $1.2 million. Whitaker proposed 72-months at$20,000 per month. The IRS countered with $20,000 monthly for a year, then increasing to $40,000 a month. But this deal required that Whitaker’s 2014 tax return had to be filed, and that estimated payments had to fix the massive withholding problem. Whitaker’s representative did not agree, and Whitaker was evidently away on a movie shoot.

In June 2015, Whitaker filed his 2014 return showing income of about $2.5M, and tax due (just for 2014) of over $800K. His wage withholding for all of 2014 was only $17K. Ten days later, the IRS made an assessment for the $800K it was owed for 2014. The IRS officer considering the installment proposal was not even aware that this return was filed, and Whitaker’s representative evidently did not let him know. Ultimately, the IRS rejected the installment plan for Whitaker’s 2013 taxes, wanting the $474,000 it was still due for 2013 taxes.

Whitaker went to court asking for relief. The Tax Court sided with the IRS, noting that Whitaker had failed to do what was required. The taxes due were not in dispute, so the only question was whether the IRS abused its discretion. The big taxes due, and the almost complete lack of wage withholding and estimated tax payments, made the case a clear one. The Tax Court agreed that the lack of estimated tax payments alone was enough reason for the IRS to say no, and that the IRS had not abused its discretion.

If Whitaker had shown that more withholding was being taken out, and made a modicum of effort to get back on track with the IRS payments, it might have been different. The Tax Court did not fault the IRS for failing to take Whitaker’s representative’s unsupported statements—for example that the tax withholding had been fixed—as true. At numerous times, the IRS asked for substantiation and yet Whitaker failed to provide it.

Finally, Whitaker appealed to the Ninth Circuit, which upheld the IRS’s actions. The case is vaguely reminiscent of boxing great Floyd Mayweather’s suit against the IRS to await his McGregor fight so he could pay his taxes. The IRS does like to get paid, but they are pretty used to granting installment agreements. Before applying for any payment agreement, of course, you must file all required tax return and cooperate. Taxpayers who need time can apply by filling out and submitting an IRS Form 9465, Installment Agreement Request and Form 433-A, and sometimes a Form 433-B. The Form 433 series of forms are basically financial statements that list all your income, expenses, and assets. 

Hindsight is 20/20 of course. But a review of these facts suggests that a realistic deal might well have been possible. The IRS would have been better off, and Whitaker would probably have been vastly better off.  Ultimately, there is no substitute for good communication, which was at least part of the problem here.

via The Tax Lawyer

False IRS Tax Returns — Personal Or Business — Can Mean Prison

You might think of criminal exposure for tax returns primarily with personal returns, not business. But here’s a reminder about business tax returns too. A Dublin, California man was sentenced to prison for filing a false corporate tax return. Shiv D. Kumar, 60, was sentenced to serve 30 months in prison, after previously pleading guilty. According to documents filed with the court, Kumar was the sole shareholder and president of A-Paratransit Inc. (API), a company that provided transportation services to disabled individuals. Kumar filed false corporate returns with the IRS for tax years 2009 and 2010, which underreported API’s gross receipts by $2,229,216 and $2,412,435, causing a tax loss of $1,584,055. Kumar deposited API’s receipts into three separate bank accounts held at different banks. To conceal API’s true income, Kumar provided his accountant with false books and records from which he had omitted gross receipts relating to two of API’s accounts. Kumar used the unreported funds for personal expenditures, including purchasing property in the Vallejo, California area. 


In addition to the term of prison, Kumar was sentenced to serve one year of supervised release. Restitution will be decided at a later date. In another case this year, a mother son duo were sentenced to prison over corporate tax returns. San Francisco residents, Howard Hsu and his mother, Tracy Chang. They were sentenced to prison after being convicted of tax fraud charges. Hsu was ordered to serve 33 months in prison, and Chang was ordered to serve 12 months and one day in prison. Hsu and Chang were found guilty by a jury of conspiring to file fraudulent corporate income tax returns, filing false tax returns, and aiding the preparation of false tax returns.

These are useful reminders that you must sign under penalties of perjury, so don’t lie on your tax return. You may never be audited, but you might be. The vast majority of tax audits are civil, and have little risk of criminal liability. Still, a majority of criminal tax cases start with a civil audit.

A claim that you do not know what is in the return may not work. In fact, the courts have consistently ruled that taxpayers have a duty to read their tax returns, to ensure that all income items are included. Since as early as 1928, courts have held that even if all data is furnished to the return preparer, the taxpayer still has a duty to read the return and make sure all income items are included. See Mackay v. Commissioner, 11 B.T.A. 569 (1928).

The feds take payroll taxes seriously too. Although most payroll tax cases do not turn criminal, the IRS views using tax money withheld from employees as stealing from the U.S. Treasury. Being being an officer or director usually means you are a responsible person, so the IRS can pursue you personally for payroll taxes if the company fails to pay. When a tax shortfall occurs, the IRS can make personal assessments against all responsible persons with ownership in or signature authority over the company. The IRS can assess a Trust Fund Recovery Assessment against every responsible person under Section 6672(a). You can be liable even if have no knowledge the IRS is not being paid. The penalty can be assessed against multiple responsible persons, allowing IRS to pursue them all to see who coughs up the money first.

The IRS also wants to make sure this kind of bad tax situation doesn’t occur again. The government can move to shut down the business so the situation doesn’t get worse. In extreme cases the government may seek criminal penalties. More commonly, if the government thinks the situation is getting worse, it can seek an injunction. Where a business gets deeper and deeper into tax debts, the practice is sometimes referred to as pyramiding.

via The Tax Lawyer

Catholic Priest Gets Prison For Tax Evasion: Don’t Lie To IRS

A Catholic priest for the Roman Catholic Diocese of San Jose, California was sentenced to 36 months in prison for tax evasion and bank fraud. The case provides cautions about how to respond to IRS questions. Father Hien Minh Nguyen, age 56, admitted that over a period of four years, he stole money from his parishioners they donated to the Diocese of San Jose. And, from 2008 through 2011, he willfully evaded paying income taxes on it. The money was for the church, but Father Nguyen admitted that he deposited it into his personal bank account. Then, he did not tell his income tax return preparer about it. He did not keep records of the donations he stole, and he filed false income tax returns that did not report the money.


In addition to the term of prison imposed, the court ordered Father Nguyen to serve three years of supervised release, and to pay a total of $1,883,883 in restitution, including $434,518 to the IRS. Father Nguyen previously pleaded guilty to tax evasion and was convicted of bank fraud following a bench trial. Before Father Nguyen admitted to the tax evasion and pleaded guilty, he was visited by the IRS, and he started talking. Agents from the IRS Criminal Investigation Division showed up unexpectedly and asked to interview him. The IRS agents said that Father Nguyen was not legally required to submit to the interview. They informed him that he had the legal right not to answer questions.

But how bad could it be, he must have thought? His first mistake was in agreeing to the interview. He should have politely taken their business cards, and said that his lawyer would call them. But Father Nguyen tried to talk his way out of the awkward situation. And as the IRS certainly noticed, Father Nguyen then proceeded to give inconsistent and conflicting answers. The IRS even asked him about his waffling responses to questions. As he may have gotten a bit rattled, Father Nguyen asked for a break. Yet even after the break, Father Nguyen went back to answering the IRS’s questions.

Once again, he gave inconsistent answers, and responses that it later become clear were replete with untrue statements. Father Nguyen’s lawyer would later claim that the IRS had tricked, deceived, or coerced the Priest. His lawyer was trying to keep out of evidence the damning statements the Priest had made to the IRS. But it was no use. The court was satisfied that the IRS had done what it was required to do, and that Father Nguyen had not been tricked, deceived, or coerced. That part of the case appears here. It is important to remember that there is a part of the IRS that is criminal. If you are visited by IRS Criminal Investigation Division Special Agents, you should consult with an attorney. You are not legally required to talk to them.

In fact, the Fifth Amendment to the U.S. Constitution guarantees your right against self-incrimination. You may believe that by answering a few simple questions you will not hurt yourself or your position–especially if you are just a witness. Don’t be so sure. Regardless of how adept you are at communication, speaking up may help the IRS build a criminal case against you. The IRS may (quite honestly) tell you that you are not the target of the investigation and merely a witness. Even so, you are entitled to retain counsel.

In the early stages of IRS criminal investigations, a person may be told he or she is a witness. You may therefore think there’s no harm in being forthcoming. You might assume your cooperation will make it more likely that the IRS will appreciate you and leave you alone. However, as the investigation continues, a witness can become a target. Even if you are convinced you are merely a witness and will remain so, the U.S. Supreme Court has ruled that you have the right to assert your constitutional privilege against self-incrimination. See Bellis v. United States.

If you are approached and questioned by a Special Agent, ask for his or her business card. Firmly but politely state that you do not want to answer any questions, and that you will have your attorney contact the Special Agent. You can fully cooperate through your attorney. This may sound paranoid, but the ramifications of getting flustered and running off at the mouth can be serious. Particularly given the fluid nature of who is a witness and who is a target, even statements you think sound innocent may not be.

via The Tax Lawyer

Trump Republican Tax Plan’s 10 Key Cuts

So far, President Trump and Republicans have not managed to repeal Obamacare. But they have moved on to the equally tough topic of tax reform, hoping for a better result. Here are ten big features of the framework released to the public.

1. Cut corporate tax rates. Corporate tax rates would be slashed from 35% to 20%. The reality is that most companies—especially big companies—do not pay the 35%. But the 20% rate would make America more competitive worldwide.

U.S. President Donald Trump speaks to members of the media after returning to the White House in Washington, D.C., U.S., on Sept. 27, 2017. Trump called the tax reform framework “a revolutionary change” that will spur economic growth and higher wages for average workers during a speech in Indiana Wednesday afternoon. It will be “the largest tax cut in our country’s history,” he said. Photographer: Zach Gibson/Bloomberg

2. Cut individual tax rates. Our current system has rates of 10%, 15%, 25%, 28%, 33%, 35% and 39.6%. They would morph into three rates of 12%, 25% and 35%. If you pay at the top, paying 35% is better than paying 39.6%. At the bottom, 12% hurts more than 10%. However, if you don’t itemize deductions, the standard deduction would double to $12,000 for individuals, and to $24,000 for married couples.

3. New Pass-through Rate. Another big change would be to reduce the tax on S corporations, partnerships and sole proprietorships to 25%. Actually, the shareholders, members or partners actually pay the tax. Instead of top individual rates of 39.6%, this plan would cap the rate owners pay on business income at 25%. If you are a successful Uber driver paying 39.6%, why not form an entity and pay 25%? Lawmakers recognize the possibility that taxpayers may try to rejigger their operations to slash their taxes from 39.6% to 25%. So, the plan says it will include “measures to prevent the recharacterization of personal income into business income to prevent wealthy individuals from avoiding the top personal tax rate.”

4. Corporate expensing. When companies buy certain assets, they are often required to claim depreciation or amortization deductions over time, even if they laid out all the cash for the purchase in the first year. A faster write-off is better, preferably all at once. Under the proposal, businesses could immediately expense the cost of certain assets. Notably, real estate would still have to be depreciated over many years. But more expensing and faster write-offs really appeal to businesses.

5. Itemized deductions. Most itemized deductions would be eliminated. Californians would be hurt by this, since the high cost of California taxes at least gets you a deduction on your federal return. However, this deduction would go under the plan. The deduction for property taxes would go, as would deductions for medical expenses. The only deductions you could claim under the proposal might be home mortgage interest and charitable contribution deductions.

6. Alternative Minimum Tax (AMT). The dreaded AMT would be eliminated. AMT may be the most insidious and counterintuitive tax there is. Even if you’re good with numbers, it’s hard to see it coming. It’s about time the AMT was repealed.

7. Federal estate tax. The federal estate tax would be eliminated too. Currently, the federal estate is imposed on estates which exceed $5.49 million. But beyond that, you pay 40%. And generation skips can taxed at 80%. President Trump has railed against the estate tax as hurting small businesses and farmers, and the tax does put a premium on planning and sophistication. So the plan would repeal it. Notably, though, the plan does not include repeal of the gift tax, which applies to transfers made during life. It also is not clear whether there would be a stepped-up basis in the decedent’s property on death for income tax purposes. So there are many details to work out in this proposed estate tax repeal.

8. Worldwide taxation. The proposal calls for a switch to a territorial system of taxation for businesses. The idea would be for U.S. companies to pay taxes on their profits to the U.S. only for amounts earned in the U.S. What about individuals? Sorry, it looks like individual Americans will still be taxed on their worldwide income, even if they live abroad and pay taxes abroad. 8 million American expats around the world with complex tax reporting and FATCA worries will evidently get no relief.

9. Repatriating Earnings. Many companies (including Apple, Microsoft, etc.) are stockpiling cash overseas in foreign subsidiaries without paying U.S. tax. The proposal would subject them to a one-time repatriation tax at a low tax rate, perhaps 10%. The actual tax rate remains unclear, so it might be less or more than 10%. And how many companies would take advantage of this remains murky too. There’s clearly more to come on this hot topic.

10. Obamacare taxes. President Trump wanted to repeal Obamacare, and its bevy of taxes. One especially burning one for wealthy investors is the 3.8% net investment income tax. But with Obamacare repeal efforts down to defeat, all these taxes remain in place. Stay tuned.


via The Tax Lawyer