Federal Income Tax Archives

Can You Still Owe Taxes on a Loan That’s 10 Years Old?

Our legal system allows people to move on from past obligations under certain circumstances. For example, people can discharge debts through bankruptcy, creditors have a limited amount of time to sue for unpaid debts, and even the IRS allows a fresh start for unpaid taxes. These laws strike a balance between allowing those who are…

Triggering Losses by Selling a Business: NQDC Example

Timing issues are one of the aspects of effective tax planning. There are scores of options for timing and tax deferral and recognition that depend on the taxpayer’s circumstances. For example, for corporate taxpayers, these timing issues may involve timing the receipt of income using the installment rules or the use of losses or foreign…

Tax Deductions for Non-Facilitating Costs for IP, M&A & Real Estate

One of the most common disputes between taxpayers and the IRS revolves around the question of whether certain expenses are deductible in the current year or need to be capitalized and recovered over time. This expense versus capitalization issue arises in various contexts. We have considered a number of these disputes on this site. It…

Charitable Tax Deductions & Bargain Sales

Our tax administration operates within the framework of a zero-sum game, leaving little flexibility for taxpayers who encounter technical foot faults or minor errors. Even when taxpayers have complied with most of the tax law requirements, a single misstep can potentially result in the disallowance of a tax benefit or deduction. This zero-sum approach, while…

Crypto Tax Loss & the Tax Loss Deduction Rules

Crypto tax loss refers to the capital losses incurred from selling or trading cryptocurrencies at a lower price than what was paid for them. These losses can be used to offset any gains earned throughout the year, reducing the taxpayer’s overall tax bill. The tax laws are clear that this type of investment loss is…

Tax Benefits of Charitable Remainder Trusts

Charitable giving is often an important part of an individual’s tax and estate planning strategy. One popular vehicle for charitable giving is a Charitable Remainder Trust (“CRT”), which can provide significant tax benefits for the donor and a stream of income for non-charitable beneficiaries during their lifetime. CRTs are valid, they can have some tax…

Explaining Real Estate Profesional Status to IRS Employees

In the complex realm of the legal system, judges hold the vital responsibility of making impartial decisions, drawing from their wealth of life experiences. These experiences, in turn, have a profound influence on the judgments they render. This principle extends to other government officials as well, such as IRS agents, auditors, and attorneys, who are…

An Appraisal is Not Always Needed for a Casualty Loss Deduction

Casualty losses are often challenged by the IRS, as they meet the “large, unusual, or questionable” (“LUQ”) standard for pulling returns for audit. On audit, the IRS insists on an appraisal from a third party that shows the difference in fair market value before and after the casualty event. Even if an appraisal is provided…

The Non-Taxable Return of Capital

Our tax laws acknowledge that a return of capital doesn’t trigger income tax. The fundamental concept is that when property is taken away from a taxpayer and then returned to them, it doesn’t result in an increase in their net worth. Rather, their net worth is restored to where it was before, and since there…

Tax Implications of Debt vs. Equity in Related Entities

Investors who engage in successful ventures often also invest in less successful ones. In some cases, one venture ends up funding another. When a taxpayer operates through multiple legal entities, this can lead to numerous complexities. For example, “due to” and “due from” intercompany transactions raise questions, even if they do not involve international transfers.…