How to Substantiate Gambling Tax Losses

There are several types of tax disputes that are frequently litigated. Gambling losses are an example. Taxpayers who gamble often incur significant losses. If the taxpayer is found to be a professional gambler, these losses can be counted for income tax purposes and used to offset the taxpayer’s other income. These tax losses can reduce…Continue readingHow to Substantiate Gambling Tax Losses

IRS Expands Sec. 9100 Relief for Late Forms 3115

As innocuous as it sounds, the Form 3115 is a tax form like no other. A Form 3115 that is inadvertently omitted from a tax return filing can result in sizable differences in tax and trigger significant tax penalties and interest. Given the amounts that are often reported on the Form 3115, errors could cost…Continue readingIRS Expands Sec. 9100 Relief for Late Forms 3115

Converting Home to Rental to Get Tax Loss Deduction

If you move out of a house and rent it to a friend for less than fair market value rent, can you then take a tax loss on the subsequent sale of the house? If the home is not converted to a rental property, the loss is disallowed as a personal tax loss. If the…Continue readingConverting Home to Rental to Get Tax Loss Deduction

Funeral Expense Organization Denied Nonprofit Status

Gargamel, the antagonist in the Smurfs, is the villain. Wile E. Coyote in the Road Runner, Raquelle in Barbie, Lex Luther in Superman, the Joker in Batman, Darth Vader in Star Wars. The list goes on. That is one side of these stories. It’s the side of the story that is presented to us. It…Continue readingFuneral Expense Organization Denied Nonprofit Status

Meal & Entertainment: The IRS Auditors “Bread & Butter”

I once worked with an IRS agent who would only make two types of adjustments. He would make UNICAP/inventory adjustments and meal and entertainment adjustments. If either of these items could be adjusted for a tax return, he would adjust them. It didn’t matter what else was listed on the tax return. It did not…Continue readingMeal & Entertainment: The IRS Auditors “Bread & Butter”

Tax on Virtual Currency Received for Microtasks

Our Federal income tax laws take a broad view of what counts as income and gain. The tax law then imposes a ridged framework for classifying and computing tax on income or gain. By casting the net wide, the tax law is able to capture just about every type of transaction that one could dream…Continue readingTax on Virtual Currency Received for Microtasks

What is a Rental Activity?

The ability to generate current year tax losses is a strong incentive for high-income taxpayers to own real estate. Real estate often produces tax losses, but not economic losses. This happens because the current operating expenses plus tax depreciation result in a current year loss. At the same time, the property likely increased in value…Continue readingWhat is a Rental Activity?

Divorce Payments & Tax Basis in Business

Our Federal income tax laws often build upon the presumption that seemingly adverse parties are actually adverse. Our tax laws do not always account for instances where the parties are actively working in concert to reduce the IRS’s cut. Transfers and payments made in relation to divorce are an example. With our tax laws, it…Continue readingDivorce Payments & Tax Basis in Business

When is Rental Real Estate a Business?

Our tax laws are not perfect. There are grey areas. Most of these grey areas are of little consequence as they do not have a significant impact on the amount of tax that is due. There are other grey areas that can significantly impact the amount of tax due. These tax disputes are frequently litigated.…Continue readingWhen is Rental Real Estate a Business?

Avoiding Tax on Discharge of a Mortgage

There are times in life when you may feel that you can’t get ahead. One step forward, two steps back–as they say. Paying income tax on debt that you avoid is an example. You negotiate with the lender or creditor and they agree to settle the balance for less. One step forward. Then a few…Continue readingAvoiding Tax on Discharge of a Mortgage

Avoiding the 60-Day IRA Rollover Requirement

If a taxpayer takes money out of their retirement account, they generally have to pay income tax on the amount distributed. What if the taxpayer wants to put the money back into the account? There have been several examples where Congress has allowed taxpayers to put money back into their accounts. The recent CARES Act…Continue readingAvoiding the 60-Day IRA Rollover Requirement

Avoid Tax by Returning Pay

There are times when a business structure or transaction no longer makes sense. This may be due to a change in the business environment, such as swings in the economy or unexpected gains or losses. It can also arise due to a change in the owners’ personal circumstances, such as a divorce or death of…Continue readingAvoid Tax by Returning Pay

Worker Reclassification: Degree of Control

The Groundhog Day movie from the 90’s starring Bill Murray portrays a news anchorman who lives the same day over and over again. He is stuck in a loop. Each day starts the same way. Bill tries to alter his conduct and he interacts with different people throughout the movie. The other characters act and…Continue readingWorker Reclassification: Degree of Control

Avoiding Gift Taxes With Formula Clauses

Congress has slowly upped the amount that can be transferred free of estate and gift taxes. This amount has changed over time. It was $1 million in 2003. It is now just over $11.5 million in 2020. This means that many people do not need to worry about estate and gift taxes. Estate and gift…Continue readingAvoiding Gift Taxes With Formula Clauses

Deducting Interest for More than One Home

The mortgage interest deduction seems simple enough. The Code provides a deduction for mortgage interest that is paid during the year. It starts with a broad grant: There shall be allowed as a deduction all interest paid or accrued within the taxable year on indebtedness. Then these 18 words in a single sentence are followed…Continue readingDeducting Interest for More than One Home

Tax Planning for Contingent Loans

Tax is often about timing. Timing issues are those where the taxpayer defers the requirement to pay taxes to a later date. Preferably a later date that is many, many years in the future. The hope is that the taxpayer can retain the amounts that would have been paid in tax today and use the…Continue readingTax Planning for Contingent Loans

Limited Partner Subject to Self-Employment Tax

When it comes to tax law, there are quite a few known-unknowns. These are tax questions that have been raised tangentially in court cases and rulings, but have not been fully answered. These situations confuse taxpayers. Tax practitioners are often asked to provide answers. The answers from tax practitioners often differ, as practitioners have different…Continue readingLimited Partner Subject to Self-Employment Tax

Tax Court Clarifies Employee Tool Plans

Prior to the Tax Cuts and Jobs Act (“TCJA”) of 2018, it was common for employers to simply pay employees more and leave it to the employees to deduct their employee business expenses on their personal income tax returns. The TCJA limited the employee’s ability to deduct employee business expenses. Many employers responded by adopting…Continue readingTax Court Clarifies Employee Tool Plans

Texas Franchise Tax: What are COGS?

With advance tax planning, it is often possible to avoid the Texas franchise tax. If the tax does apply, it can often be minimized by a close reading and application of the rules. The recent Sunstate Equipment Co., LLC vs. Comptroller of Public Accounts, No. 17-0444 (Tex. 2020) case provides an opportunity to consider when…Continue readingTexas Franchise Tax: What are COGS?

S Corp Election Terminated by Standard LLC Language

If you make an S corporation election and do not fix the standard language that is typically included in the LLC company agreement, you’ll void the S corporation election. This is an issue that is usually identified by during an audit by the IRS. Many taxpayers overlook this issue until it is too late (it…Continue readingS Corp Election Terminated by Standard LLC Language

The Late Mark-to-Market Election

Those who trade stocks can take advantage of the mark-to-market election to convert capital losses into ordinary losses. This election is only available to “traders.” There are often questions as to when a taxpayers trading activities are sufficient to warrant being treated as a “trader” for tax purposes. By the time the taxpayer discovers that…Continue readingThe Late Mark-to-Market Election

Tax Loss Planning: The At-Risk Rules

Are you purchasing a business or real estate that involves financing a business or investment that is likely to produce tax losses in the future? Or have you already made the purchase? If so, there may be ways to ensure that you can take the loss in the future. To do so, you have to…Continue readingTax Loss Planning: The At-Risk Rules

Can “Business Synergies” be an Asset that Increases a Tax Loss?

The tax consequence of a transaction often depends on how one characterizes or describes the transaction. Business synergies are often cited as the rationale for merger and acquisition deals. In a M&A deal, are “business synergies” a separate asset for tax purposes? Can you list “business synergies” as a separate asset and then take a…Continue readingCan “Business Synergies” be an Asset that Increases a Tax Loss?

Big Tax Savings With ESOP, But Requires Work

An employee stock ownership plan (ESOP) can produce significant income tax savings. This tax savings isn’t exactly free. One has to keep up with the ESOP and the relevant rules to ensure that the tax savings are achieved. This compliance work is required and failure to comply can be costly. The recent Ed Thielking v.…Continue readingBig Tax Savings With ESOP, But Requires Work

Tax Planning for the Start-up Limitation Rules

Our tax laws include start-up rules that limit the ability to deduct certain business and investment expenses. For business owners and investors with other sources of income, this can result in funds being sent to the IRS to pay taxes at a time when the capital is needed to fund the business or investment growth.…Continue readingTax Planning for the Start-up Limitation Rules

Loan to an S Corporation to Allow Tax Loss

Tax basis can limit a shareholder’s loss from an S corporation. If an S corporation has a tax loss but the shareholder doesn’t have sufficient tax basis to take the loss, the shareholder will typically have to loan money to the S corporation. This tax debt basis makes the loss allowable in the current year.…Continue readingLoan to an S Corporation to Allow Tax Loss

Tax on Payment for Being Born With Medical Condition

We can do some amazing things given the state of our science and technology. These advances lead to some interesting tax questions. The IRS recently addressed such a question in PLR 201950004. It considers whether damages paid by a fertility clinic for failing to perform a genetic test are excluded from the recipient’s income as…Continue readingTax on Payment for Being Born With Medical Condition

Sale of Trailers Doesn’t Qualify for Installment Sale Treatment

If you buy, subdivide and sell real estate, can you seller-finance the sales and report the gain over a long period of time? The answer is generally yes, but advance planning is needed. The court addresses this in Joyner Family Limited Partnership v. Commissioner, T.C. Memo. 2019-159. Facts & Procedural History The taxpayers purchased land…Continue readingSale of Trailers Doesn’t Qualify for Installment Sale Treatment

Bad Debt Tax Deduction for Guarantee Payment?

If you guarantee a loan for a third party and have to make payments due to the guarantee, do you get to deduct the payment as a bad debt for tax purposes? The court addresses this in Baker Hughes, Inc. v. United States, No. 18-20585 (5th Cir. 2019) in the context of a payment made…Continue readingBad Debt Tax Deduction for Guarantee Payment?

Sale of Long-Term Service Contracts: Capital or Ordinary Gain?

If a taxpayer sells a business that owns long-term service contracts, is the gain attributable to the contracts subject to tax at ordinary or capital gains rates? The IRS’s recent action on decision for the Greenteam Materials Recovery Facility PN v. Commissioner, T.C. Memo. 2017-122 court case deals with this in the context of a…Continue readingSale of Long-Term Service Contracts: Capital or Ordinary Gain?

The IRS Recent Focus on S Corp Owners

The IRS has announced several new compliance campaigns focusing on S corporations. This is needed as the audit rate for S corporation is extremely low. The most recent IRS compliance campaign focuses on shareholder stock basis issues for S corporation owners. Those who have significant S corporation losses or large distributions should take time to…Continue readingThe IRS Recent Focus on S Corp Owners

Travel Expenses Allowed for Repetitive Pattern of Travel

The IRS frequently challenges travel expenses.  These expenses have a higher substantiation requirement, which the IRS uses to disallow every expense no matter how reasonable or how certain it is that the expense was incurred.  But what if it was exceedingly certain that the expense was incurred and there is a method for computing the…Continue readingTravel Expenses Allowed for Repetitive Pattern of Travel

Records Needed for Partial Asset Dispositions

Taxpayers often overlook “partial asset dispositions.” Their tax advisers do too. This may be due to it being a depreciation issue that seems unimportant. It may also be that the partial asset disposition is a relatively new concept. Regardless, partial asset dispositions can save taxpayers quite a bit in taxes (it is a timing issue,…Continue readingRecords Needed for Partial Asset Dispositions

Using Warrants to Make Future Purchases of S Corporation Stock

Can you make a gift to charity but retain the right to pull back the value of the gift in the future, and still get a charitable deduction for the gift? The court said “no” in In Re Stapley, No. 09-47699 RLE (Bankr. N.D. Cali. 2019). The failed tax shelter included an S corporation whose…Continue readingUsing Warrants to Make Future Purchases of S Corporation Stock

Can the IRS Ignore the Legal Existence of a Corporation?

If a taxpayer forms a legal entity and it is taxed as a C corporation, can the IRS disregard the legal existence of the corporation and assess the corporation’s tax to the owner? The court addresses this in Russell v. Commissioner, T.C. Memo. 2019-146. Facts & Procedural History The taxpayer filed his personal income tax…Continue readingCan the IRS Ignore the Legal Existence of a Corporation?

The Timing Trap: Failed Installment Sales

What happens if you sell an asset and are to receive payments in the future, but your accountant fails to elect the installment method? Do you have to report the full amount of the gain in the year of sale? What happens if the buyer fails to make the payments in subsequent years? The IRS…Continue readingThe Timing Trap: Failed Installment Sales

M&A Finders Fee Not Deductible for Acquirer

If a company acquires another company and pays a finders fee to the party who connected the two for the sale, is the finders fee deductible by the acquirer? This question touches on whether an expense is deductible if the real benefit is to another company. The court addresses this in Plano Holding LLC v.…Continue readingM&A Finders Fee Not Deductible for Acquirer

Can the IRS Collect Gift Tax From Recipient After 14 Years?

If someone gives you property and then dies and more than ten years has passed since the gift, can the IRS sue you to collect the amount of the gift from you? Most would think the answer is a resounding “no,” as the recipient isn’t liable for unpaid gift taxes and the statute of limitations…Continue readingCan the IRS Collect Gift Tax From Recipient After 14 Years?

Avoiding State Income Tax on Part-Time Residents

Sometimes you can’t avoid paying state income taxes. This is true for those who have no ties to any state other than a state that has an income tax. But for those who have ties to multiple states, they can often structure their affairs to avoid the state income tax. This can be difficult to…Continue readingAvoiding State Income Tax on Part-Time Residents

S Corp Conversions: Watch out for Disappearing AAA

Small and medium-sized business can save quite a bit in taxes by using S corporations. But with this tax savings comes complexity. This complexity comes from how S corporations flow through profit and have the profit taxed on the individual owner’s personal tax return. The rules for tracking this are, well, lacking. Accountants are often…Continue readingS Corp Conversions: Watch out for Disappearing AAA

Final Regulations Issued: Leveraged Partnership Distributions Still Viable

The “leveraged partnership distribution” or “disguised sale” is a common tax savings technique used by real estate owners. Taxpayers pushed the envelope with these transactions by using “bottom dollar guarantees.” This led to guidance from the government making it more difficult to benefit from leveraged partnership distributions. The Treasury recently finalized regulations that say what…Continue readingFinal Regulations Issued: Leveraged Partnership Distributions Still Viable

The Broad Reach of the Economic Substance Doctrine

Congress provides tax incentives to change taxpayer behavior. If a taxpayer changes their behavior to take advantage of the incentive, they have to do so carefully. The IRS and the courts can apply the economic substance doctrine to take away the tax benefit. This doctrine can apply to more transactions than what one would consider…Continue readingThe Broad Reach of the Economic Substance Doctrine

Documenting the Sec. 199a Rental Real Estate Safe Harbor

We have previously considered the “trade or business” requirement for the Section 199a deduction. The government recently issued guidance to clarify when rental real estate activities can qualify for the deduction. While the guidance is needed, it adopts a record keeping requirement that effectively prevents most rental real estate activities from ever qualifying for the…Continue readingDocumenting the Sec. 199a Rental Real Estate Safe Harbor

Avoiding Hobby Loss Limits for Long-Term Projects

Long-term projects often lose money. They often do so for several years. This is the result of a project that needs capital to build infrastructure or to develop a new market or to capture market share. Taxpayers may be disappointed to learn that the tax losses coming from these long-term projects in the early years…Continue readingAvoiding Hobby Loss Limits for Long-Term Projects

Bad Debt Deduction for Real Estate Lender for Non-Real Estate Loan

If a taxpayer regularly makes real estate loans from their personal accounts, they would be entitled to a bad debt deduction for loans that are not repaid. But what if they venture beyond real estate loans and make a single non-real estate loan? If the non-real estate loan goes bad, can they deduct the bad…Continue readingBad Debt Deduction for Real Estate Lender for Non-Real Estate Loan

Court Addresses Tax Losses from Short-Term Rentals

Short-term rental properties are more popular than ever. Online services like Airbnb have made this possible. But how are tax losses from short-term rentals handled? Can the taxpayer use the rental losses to offset their non-rental income for tax purposes? The court addresses one aspect of these rules in Eger v. United States, 18-cv-00199-DMR (N.D.…Continue readingCourt Addresses Tax Losses from Short-Term Rentals

Court’s Take on How to Avoid the Interest Expense Limitation

Interest one pays is generally deductible for income tax purposes. For real estate owners who borrow against the value of their properties, the interest expense deduction is often one of their largest tax deductions. This tax deduction can be limited. The court in Lipnick v. Commissioner, 153 T.C. 1 highlights how one might avoid this…Continue readingCourt’s Take on How to Avoid the Interest Expense Limitation

The Importance of Accounting for C Corporation Expenses

It is important to keep accurate books and records. Accurate books and records can result in significant tax savings. This is particularly true for entrepreneurs who own more than one business. When one or more of these businesses are taxed as a C corporation, the stakes can be even higher. The Nzedu v. Commissioner, T.C.…Continue readingThe Importance of Accounting for C Corporation Expenses

IRS & the Burden to Prove Constructive Dividends

When a C corporation pays expenses for its shareholder, the payment can be subject to income tax for the shareholder as a constructive dividend. One defense is that the expenses for the C corporation were legitimate. Does the taxpayer have to prove the amount of the expenses or does the IRS? The Combs v. Commissioner,…Continue readingIRS & the Burden to Prove Constructive Dividends

Taxpayer Cannot Recoup Attorney Travel Costs

If the IRS wrongfully denies your refund claim and you are successful in litigating the matter in court, you are entitled to recoup some of your court costs. But what about the taxpayer’s tax attorney’s travel costs? And what if the travel costs were necessary as the tax issue was complex and a tax attorney…Continue readingTaxpayer Cannot Recoup Attorney Travel Costs

Can the IRS Get Records from Foreign Corps that do Business in the U.S.?

In CCA 2019060408545121, the IRS asked its tax attorneys whether a foreign corporation that conducts business with a limited partner in the U.S. had to produce records.  Our tax laws provide address this very topic, as noted in the CCA. The CCA serves as a reminder that failing to provide records for transactions with foreign…Continue readingCan the IRS Get Records from Foreign Corps that do Business in the U.S.?

Reporting Debt Discharged in a Court Settlement to the IRS

There are some circumstances where information has to be reported to the IRS, even though the information does not trigger a tax. But the potential problem can be that the information reporting triggers an IRS audit or other consequences. The Form 1099-C, Cancellation of Debt, form can have this effect. In PLR 201927005 the IRS…Continue readingReporting Debt Discharged in a Court Settlement to the IRS

Voluntary Sale In Advance of Forced Auction an Involuntary Conversion?

A taxpayer can generally avoid paying income tax on gain from the sale of property if the sale is an involuntary conversion. This typically involves a government act that takes or destroys the taxpayer’s property. There are a number of different types of property and takings that can qualify? But what about a local TV…Continue readingVoluntary Sale In Advance of Forced Auction an Involuntary Conversion?

Recouping Tax on Marital Wages Repaid to Employer After Divorce

If a couple files a joint return and pays tax on the income they earn, but after they divorce it turns out that one of the spouses has to repay monies received in error, can the other spouse recoup their portion of the prior tax paid on the income? The claim of right doctrine may…Continue readingRecouping Tax on Marital Wages Repaid to Employer After Divorce

Does an Author Pay Self-Employment Tax on Royalties?

Taxpayers are free to structure payments for services rather than for something other than services. This can save self-employment taxes. But can a taxpayer carve out part of their service income by asserting that some part of the income is not from a business? The Slaughter v. Commissioner, T.C. Memo. 2019-65, case addresses this in…Continue readingDoes an Author Pay Self-Employment Tax on Royalties?

What if the IRS Violates the Law?

What happens if the IRS violates the law? Specifically, what if the IRS assesses a penalty and attempts to collect it without first issuing the proper notice to the taxpayer? The court addresses this in Romano-Murphy v. Commissioner, 152 T.C. 62, in the context of a trust fund recovery penalty. Facts & Procedural History The…Continue readingWhat if the IRS Violates the Law?

LLC Cannot Use Crewman’s Exemption for Employment Taxes

Can a U.S. citizen who owns and operates a vessel outside of the U.S. avoid paying U.S. employment taxes for its crewmen by using a foreign legal entity? The court considered this issue in DAF Charters LLC v. Commissioner, 152 T.C. 14, for a single member LLC formed in the U.S. that was owned by…Continue readingLLC Cannot Use Crewman’s Exemption for Employment Taxes

Non-Taxable Subsidy or Taxable Benefit?

Some payments are not subject to Federal income tax. State subsidies are an example. But what is the difference between a non-taxable subsidy and a taxable benefit? The court addresses this in Ginsberg v. United States, No. 2018-1788 (Fed. Cir. 2019), in the context of the New York state brownfield tax credit. Facts & Procedural…Continue readingNon-Taxable Subsidy or Taxable Benefit?

IRS Not Limited in Collecting Restitution Assessments

The IRS is authorized to assess criminal restitution for certain tax crimes. This process allows the IRS to collect the criminal restitution as if it was a tax. The law authorizing these collections is relatively new and evolving. The recent Carpenter v. United States, 152 T.C. 12, case highlights why it is important for those…Continue readingIRS Not Limited in Collecting Restitution Assessments

Can Gambling Losses be Deducted as Casualty Losses?

If a taxpayer cannot deduct gambling losses given the restrictions on gambling losses, can they deduct them as casualty losses instead? What if the gambling loss are attributable to prescription medications known to cause compulsive gambling? The court addresses this in Mancini v. Commissioner, T.C. Memo. 2019-16. Facts & Procedural History The taxpayer diagnosed with…Continue readingCan Gambling Losses be Deducted as Casualty Losses?

The Sec. 179D Government-Owned Building Allocation

Section 179D provides an incentive for building owners to install energy efficient systems. The IRS released CCA 2018-005, which addresses one of the controversial aspects of Sec. 179D–namely, the ability for government building owners to allocate the deduction to the designer of the energy efficient property. About Section 179D Section 179D was enacted in 2005,…Continue readingThe Sec. 179D Government-Owned Building Allocation

How to Allocate Tax Basis for Real Estate

If you sell real estate, you pay tax on the gain. Gain is the product of the sales price less tax basis. Tax basis in turn is the amount invested in the property. But how do you calculate and then prove tax basis for buildings located on the property when you sell some but keep…Continue readingHow to Allocate Tax Basis for Real Estate

Is Election to Waive NOL Carryback Irrevocable?

You have to be careful when electing to waive the right to carry back a net operating loss. This is particularly true if there are items on your tax returns from earlier years that the IRS may eventually adjust if audited. The Bea v. Commissioner, No. 18-10511 (11th Cir. 2019), case provides an example of…Continue readingIs Election to Waive NOL Carryback Irrevocable?

Research Tax Credit Records Must Be Kept for 40+ Years

A frequent question is how long one has to keep records for tax purposes. The United States v. Quebe, No. 3:15-cv-294 (S.D. Ohio 2019) case provides the answer for research tax credits. The answer is that you have to keep records that pre-date the formation of your business by twenty years and then you have…Continue readingResearch Tax Credit Records Must Be Kept for 40+ Years

How to Correct Late Accounting Method Changes

A consistent mistake on a tax return for more than two years may require an accounting method change to correct. The IRS has procedures for making these elections, which generally require a timely filed tax return. But what if you miss the filing deadline–are you out of luck? Private Letter Ruling (“PLR”) 201850013 provides the…Continue readingHow to Correct Late Accounting Method Changes

Can Defective Deed Defeat IRS Estate Tax Lien?

The IRS lien is broad and attaches to the taxpayer’s property. Creative tax attorneys have tried to find ways around the lien with limited success. The recent Saccullo v. United States, No. 17-14546 (11th Cir. 2019) case raises the question as to whether a defectively executed deed be used to defeat the IRS’s estate tax…Continue readingCan Defective Deed Defeat IRS Estate Tax Lien?

Can Foreign Government Use U.S. Court to Collect From U.S. Person?

If a U.S. person commits tax fraud under the laws of a foreign county, can the foreign country’s tax collector use the U.S. court system to collect from the U.S. person? The court recently addressed this in In re SKAT Tax Refund Scheme Litigation, No. 18-md-2865 (LAK) (S.D.N.Y. 2019). Facts & Procedural History The plaintiff…Continue readingCan Foreign Government Use U.S. Court to Collect From U.S. Person?

Retaining Rights With a Charitable Conservation Easement

Conservation easements can result in significant charitable deductions for real estate owners and investors. But can an owner or investor retain rights to the property and still get the charitable deduction. The courts continue to define when this is possible. The Pine Mountain Preserve LLLP v. Commissioner, 151 T.C. 14, case is the latest case…Continue readingRetaining Rights With a Charitable Conservation Easement

Appropriate a Book of Business, Capital or Ordinary Gain?

If an investment advisor is terminated by the bank he works for and the bank keeps the advisors book of business, is the bank compensating the investment advisor for the sale of his book of business or is it paying compensation for services? One would seem to produce capital gain and the other ordinary gain.…Continue readingAppropriate a Book of Business, Capital or Ordinary Gain?

IRS Can Collect Father’s Tax Restitution from Son

The rules that allow the IRS to assess and collect criminal restitution as if it is a tax due present some unique questions.  In Bontrager v. Commissioner, 151 T.C. 12, the court considered whether the IRS can assess and collect a father’s tax restitution payment as tax restitution against the son.   Facts & Procedural History…Continue readingIRS Can Collect Father’s Tax Restitution from Son

Court Clarifies Inventory Capitalization Rules for Producers

There are a few items that are low hanging fruit that make for easy adjustments for IRS auditors.  The adjustment for indirect costs is an example of such an adjustment that can be made for any taxpayer that has inventory.  The recent Patients Mutual Assistance Collective Corporation v. Commissioner, 151 T.C. No. 11 (2018), case provides…Continue readingCourt Clarifies Inventory Capitalization Rules for Producers

Early IRA Distribution, Gambling Not a Disability

Early distributions from IRAs are subject to a 10 percent additional tax.  The 10 percent additional tax does not apply if the distribution is taken when the IRA owner is disabled.  The recent Gillette v. Commissioner, T.C. Memo. 2018-195, case addresses whether medically-induced compulsive gambling qualifies as a disability. The Facts & Procedural History The taxpayer-wife is a…Continue readingEarly IRA Distribution, Gambling Not a Disability

Planning for Tax Deductible Entertainment Expenses

Entertainment expenses are deductible but the deduction is limited to 50 percent of the amount spent. There have been a number of disputes between taxpayers and the IRS as to what counts as a limited entertainment expense. The law was recently changed such that entertainment expenses are no longer deductible.  This change to full disallowance…Continue readingPlanning for Tax Deductible Entertainment Expenses

U.S. Taxpayer With U.S. Residence Cannot Exclude Foreign-Earned Income

There are a number of tax issues that U.S. citizens and residents who live abroad have to consider.  One of these is whether they qualify to exclude their foreign-earned income in computing U.S. income taxes.  This exclusion has resulted in a number of tax disputes.  The Leuenberger v. Commissioner, T.C. Summary Opinion 2018-52, case addresses the…Continue readingU.S. Taxpayer With U.S. Residence Cannot Exclude Foreign-Earned Income

Documenting Tax Losses for Worthless Securities

Tax losses for worthless securities are often challenged by the IRS.  It particularly important to document the loss.  There are several elements taxpayers have to establish to secure the benefit of tax losses for worthless securities.  The recent Giunta v. Commissioner, T.C. Memo. 2018-180, case provides an opportunity to consider these elements. Facts & Procedural History The…Continue readingDocumenting Tax Losses for Worthless Securities

Court May Explain How to Allocate Tax Basis to Intangible Assets

If the U.S. government allows a taxpayer to call a liability an asset and then acts to make the asset worthless, can the taxpayer take a tax loss for the loss of the so-called asset?  The Citigroup, Inc. v. United States, No. 15-953T (Ct. Cl. 2018) court case addresses this fact pattern.  The case gets to one…Continue readingCourt May Explain How to Allocate Tax Basis to Intangible Assets

Donations to Pastor are Taxable Income, Not Gifts

The distinction between taxable compensation and non-taxable gifts comes up in a number of contexts and has led to a number of tax disputes.  Severance payments made to workers are an example.  The recent Felton v. Commissioner, T.C. Memo. 2018-168, court case addressed this issue in the context of segregated donations made by a congregation…Continue readingDonations to Pastor are Taxable Income, Not Gifts

Planning for Start-Up Businesses, Yacht Rental Example

New businesses may not be immediately profitable.  To help mitigate the financial risk, many businesses are started by workers who have a day job.  If the business is not immediately profitable it can help the owner finance the business if the owner is able to use the tax losses from the business to offset the…Continue readingPlanning for Start-Up Businesses, Yacht Rental Example

Income Earned by Child Taxed to Parent

If a minor child earns income, is the income taxable to the parent or the child?  There have been quite a few tax disputes involving this question.  The Ray v. Commissioner, T.C. Memo. 2018-160 court case provides an opportunity to consider these rules. The Facts & Procedural History Mr. Ray the financial officer for a non-profit…Continue readingIncome Earned by Child Taxed to Parent

Conservation Easement Denied for Private Golf Course

Tax benefits can cause investors to put money were they otherwise would not.  The conservation easement is one example.  Conservation easements reward investors with charitable deductions for putting money into projects that conserve real property.  The charitable deductions can be very large in relation to the amount invested.  The recent Champions Retreat Golf Founders, LLC v.…Continue readingConservation Easement Denied for Private Golf Course

Line of Credit Standby Fees, to Deduct or to Capitalize?

Many businesses rely on a standby line of credit to cover their expenses, to weather downturns, and to grow.  But this credit can be expensive in terms of interest and fees. The fees can be problematic as they may not be deductible for federal income tax purposes at the time they are paid.  The IRS…Continue readingLine of Credit Standby Fees, to Deduct or to Capitalize?

Court Says Partnership is Worth Less, Not Entirely Worthless

The IRS often challenges tax loss deductions.  In many cases, it does so by challenging the year in which the loss is allowable.  It can be difficult to determine which year the loss should be taken.  When an asset is losing value over time, there is a time when the asset is worth less than…Continue readingCourt Says Partnership is Worth Less, Not Entirely Worthless

Intercompany Fee Arrangement Lacks Economic Substance

If the employees and owners of a profitable C corporation set up a related entity and lease the employee-owner’s services back to the C corporation, can the C corporation deduct the payments?  Taking it a step further, what if the related entity is owned by a retirement plan so that most of the payments by…Continue readingIntercompany Fee Arrangement Lacks Economic Substance

The Trade or Business Requirement for the Sec. 199A Deduction

The new Sec. 199A deduction that provides a 20 percent benefit for flow through entities has been in the news as of late.  The Yaryan v. Commissioner, T.C. Memo. 2018-129, case provides an opportunity to consider one aspect of this new Sec. 199A deduction.  Specifically, the Treasury released regulations that adopt a “trade or business” standard…Continue readingThe Trade or Business Requirement for the Sec. 199A Deduction

Litigation Award for Damage to Dairy Farm Ordinary Not Capital

If a dairy farmer receives an award for damages to the farm, is the damage award capital or ordinary?  The distinction is important.  Unlike ordinary income, capital gains are generally afforded lower tax rates and not subject to self-employment taxes.  The court considered this fact pattern in Allen v. United States, No. 16-C-1412 (E.D. Wis. 2018). Facts &…Continue readingLitigation Award for Damage to Dairy Farm Ordinary Not Capital

FBAR Not Limited to $100,000, Willfulness Upheld

There have been a number of recent court cases involving foreign bank account or FBAR reporting penalties.  This is likely due to the significant amount of the penalty and that many do not fully appreciate the amount of the liability they face if caught not complying with the FBAR rules.  The recent Norman v. United…Continue readingFBAR Not Limited to $100,000, Willfulness Upheld

Avoiding Cancellation of Debt Using Rebates or Refunds

Can taxpayers avoid cancellation of debt income by structuring debt reductions as rebates or refunds?  The court touched on this issue in French v. Commissioner, T.C. Summary Opinion 2018-36. The Facts & Procedural History The taxpayers borrowed money to purchase a home.  When they failed to make their payments on the mortgage, the bank made contacted…Continue readingAvoiding Cancellation of Debt Using Rebates or Refunds

Legal Construction: Taxes Tied to Activities

When Congress provides a tax benefit contingent on some activity, there is often a question as to whether the activity can be read broadly to encompass many sub-activities or has to be read narrowly.  This impacts the amount of the tax benefit and how difficult it is to comply. Generally, if construed broadly, the tax…Continue readingLegal Construction: Taxes Tied to Activities

The Statutory Employee Classification Post-TCJA

The Tax Cuts and Jobs Act (“TCJA”) made several changes to our tax laws. One such change is that employees are no longer able to deduct unreimbursed expenses incurred as an employee. Given this change, employers and their workers may need to re-evaluate their relationship. For some workers, this may mean re-evaluating whether the worker…Continue readingThe Statutory Employee Classification Post-TCJA

Guaranteeing a Loan for Your S Corporation

In Phillips v. Commissioner, No. 17-14439 (11th Cir. 2018), the court concluded that a judgment against the owner of an S corporation for guaranteeing the business debts does not increase the owners tax basis in the S corporation.  This is one area where a little advance planning can go a long way to avoiding a tax…Continue readingGuaranteeing a Loan for Your S Corporation

Deducting Fringe Benefits for Family Members

Small business owners often look for ways to reduce their taxes.  With family businesses, these plans often involve employing the owner’s children.  This raises the question of whether a small business owner employ their children as independent contractors and deduct seemingly personal expenses for the children as fringe benefits if the children did in fact…Continue readingDeducting Fringe Benefits for Family Members

Credit for Employment Taxes Reported in Error for Another Entity

If employment taxes are paid by one legal entity but incorrectly reported to the IRS for another legal entity, can the entity that paid the taxes get credit for the payment? The IRS said ‘no;’ the U.S. Tax Court said ‘yes.’ The case is E.C.C.B.A. v. Commissioner, T.C. Memo. 2018-55. Facts & Procedural History The case…Continue readingCredit for Employment Taxes Reported in Error for Another Entity

Establishing Tax Basis in IRA Contributions

Contributions to IRAs are deductible.  If not deductible, the taxpayer has basis in his IRA so that this amount is not taxable when taken out of the IRA.  The idea is that the taxpayer probably paid income taxes on the money prior to putting it into the IRA and should not be taxed on it…Continue readingEstablishing Tax Basis in IRA Contributions

What is a Real Estate Trade or Business?

There are a lot of questions about the new Sec. 199A pass thru deduction.  One question is whether real estate will qualify as a trade or business.  Since it is not defined in Sec. 199A, general tax law will apply.  There are a number of court cases on point.  The court recently issued its opinion…Continue readingWhat is a Real Estate Trade or Business?

Documenting Loans to Closely-Held Corporations

In Norgaard v. United States, No. 16-12107-FDS (D. Mass. 2018), the court addressed whether a personal loan made to a closely held corporation can be deducted as a bad debt when the business goes out of business. The case highlights why it is important to document loans made to corporations. The Facts & Procedural History…Continue readingDocumenting Loans to Closely-Held Corporations

Limited Window of Time to Structure Divorce Settlements

The tax deduction and income provisions for alimony have been repealed for divorce decrees entered into after December 31, 2018 or for earlier divorces where the agreements are modified after that date. This gives married couples and formerly married couples a window of time to structure or restructure their agreements to reduce their overall taxes.…Continue readingLimited Window of Time to Structure Divorce Settlements

Misappropriated Money Subject to Tax, Even if No Criminal Violation

The proceeds of criminal activities are taxable income. Money that is embezzled from an employer is taxable to the embezzling employee. But what about money transferred between friends with the agreement that one of them will invest the funds, but he instead uses the funds personally and in doing so did not violate a criminal…Continue readingMisappropriated Money Subject to Tax, Even if No Criminal Violation

Court: IRS Cannot Apply New Law Based on Conduct Predating the Law

In Rafizadeah v. Commissioner, 150 T.C. No. 1 (2018), the court concluded that the IRS made a late assessment of tax and penalties. The case turns on whether the IRS can benefit from the longer six-year assessment period based on an information return filing that the law did not obligate the taxpayer to make at…Continue readingCourt: IRS Cannot Apply New Law Based on Conduct Predating the Law

Family Cattle Operation Denied Tax Deductions

In Barnhart Ranch Co. v. Commissioner, No. 16-60834 (5th Cir. 2017), the court considered who was entitled to deduct expenses for cattle that were descended from cattle the taxpayers inherited and other cattle that were subsequently purchased. The case shows how important it is to implement an accounting system to capture income and expenses in…Continue readingFamily Cattle Operation Denied Tax Deductions

Payments to Foreign Student Studying in U.S. Subject to Tax

We get quite a few questions from students who are in the U.S. on student visas as to whether their research awards are taxable in the U.S.  The answer depends in large part on the terms of the applicable tax treaty and whether the awards are compensation for services or pure grants. The recent Dovzhenok…Continue readingPayments to Foreign Student Studying in U.S. Subject to Tax