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

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?

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

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?

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

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?

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 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

IRS Rejects Court’s Passive Activity Loss 5% Owner and Grouping Decision

The passive activity loss (“PAL”) rules can limit the ability to deduct losses from passive activities, such as rental losses.  The real estate professional and activity grouping rules can allow taxpayers to avoid having their losses limited by the PAL rules.  Earlier this month, the IRS issued AOD  2017-007, IRB 2017-42 , to note its formal…Continue readingIRS Rejects Court’s Passive Activity Loss 5% Owner and Grouping Decision

Court Says Deduction for Tax Loss Not Allowed for Worthless Debt

Tax losses for worthless debts often trigger IRS audits. On audit, it is common practice for the IRS to disallow the losses based on the debt not being worthless, the amount of the loss not being correct, and that the taxpayer took the loss in the wrong tax year. Taxpayers can take steps to limit…Continue readingCourt Says Deduction for Tax Loss Not Allowed for Worthless Debt

Subchapter S Corporation Losses Limited by Tax Basis

One of the benefits of Subchapter S corporations is the ability to have losses flow through from the business’ tax return to the individual shareholder’s tax return. These flow-through losses are limited by the shareholder’s tax basis in the S corporation stock. The court recently addressed this limitation in Tinsley v. Commissioner, T.C. Summary Opinion…Continue readingSubchapter S Corporation Losses Limited by Tax Basis

Bad Credit Results in Disallowance of Bad Debt Deduction

The IRS often challenges bad debt deductions–particularly when the loan is from a family member or friend.  The courts have developed several factors that they consider in these disputes.  One of these factors is whether the borrower would have been able to secure a loan from a third party.   The court recently addressed this in…Continue readingBad Credit Results in Disallowance of Bad Debt Deduction

Bad Debt Deduction for Cease-and-Desist Order

With tax losses, one challenge is to determine what tax year the loss is allowable.  The loss year is usually identified by a triggering event.  Is a cease-and-desist order from the state regulator a triggering event that establishes that a start-up company is worthless in the year the order was received?  The court addressed this in Sensenig…Continue readingBad Debt Deduction for Cease-and-Desist Order

Grouping Nonpassive Activities Under the PAL Rules

Taxpayers are often surprised to learn that some losses may not be netted against gains in the current tax year. This is often due to the passive activity loss and material participation rules. The IRS National Office addressed these rules in TAM 201634022, in the context of whether two businesses should be grouped together and…Continue readingGrouping Nonpassive Activities Under the PAL Rules

Tax Deductions for Hobby Survives IRS Scrutiny

There are quite a few cases where the IRS disallowed loss deductions for “hobbies.” There are also quite a few cases where the courts have upheld the IRS’s position. These cases are decided based on the facts and how the courts interpret these facts. The facts in Main v. Commissioner, T.C. Memo. 2016-127, provide a…Continue readingTax Deductions for Hobby Survives IRS Scrutiny

Bad Debt Deduction Not Allowed Until Business Fails

If you lend money to a failing business and the business eventually fails, can you take a bad debt deduction?  And if so, when?  The U.S. Tax Court addressed this in Cooper v. Commissioner, 143 T.C. 10, which provides an opportunity to consider the question. Facts & Procedural History The Coopers started Pixel in 1983.  Pixel…Continue readingBad Debt Deduction Not Allowed Until Business Fails

The Hobby Loss Rules: Planning for Unprofitable Businesses

Ordinary and necessary expenses incurred in operating a business are deductible against Federal income tax.  This is even true for side gigs or moonlighting work.  The IRS frequently challenges these deductions if the activity does not produce a profit.  The recent Jones v. Commissioner, T.C. Summary Opinion 2007-21, court case provides an opportunity to consider these rules.…Continue readingThe Hobby Loss Rules: Planning for Unprofitable Businesses