Federal Income Tax Archives

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.…

Recovering Taxes Paid for Another Party

If you pay tax for another party, can you recover the payment if the tax is not owed? The answer is generally “no,” as you cannot sue the Federal government unless it consents and it only consents in limited circumstances. One such consent is the ability to sue for a refund. The rules that allow…

IRS Guidance on Structuring Attorneys Fees

It should not be a surprise to learn that attorneys often hire tax attorneys to help them minimize their taxes. One popular tax savings strategy for attorneys is to structure their contingent fees. A contingent fee is a payment arrangement in which a lawyer provides services on the condition that payment will only be made…