Forget the 5-Year Rule – Change Entity Classification Early

Many believe that once you elect an entity’s tax classification, you are locked into that choice for at least 5 years. Conventional wisdom says that the tax status cannot be changed within a 5-year or 60-month period. However, a recent IRS private letter ruling shows this is not necessarily the case. In PLR 202341001, the…

Breach of Contract as Theft Loss Tax Deduction

Many people have experienced the pain of an investment gone wrong. You put money into a business, loan funds to a friend, or participate in a real estate venture, expecting strong returns. But instead of profits, you end up suffering losses when the deal unravels. It leaves you wondering – can I at least deduct…

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…

The Evolution of Foreign Account Tax Reporting

The IRS and Treasury face a number of challenges in administering our tax and financial systems. This includes challenges presented by foreign transactions by U.S. citizens and residents. In recent years, high-profile cases involving Americans using offshore accounts to evade taxes have prompted the U.S. government to crack down on tax evasion and make it…

Recovering Legal Expenses for Mistaken IRS Audit of Non-Resident

The U.S. has significant and complex reporting and filing and notice requirements. This includes a myriad of state and local requirements and federal requirements, including income tax return filing requirements. As odd as it sounds, it is part of what makes America great. We often don’t think about it, but these filing requirements are part…

Buy-Sell Agreements & Perils of the Estate Tax

Taxes punish success. They are a consequence of hard work or, in some cases, ingenuity. Even seemingly common business transactions can trigger this type of punishment, and the consequences can be sizeable. This is especially true when it comes to the Federal estate tax. The tax itself can amount to 40% of the value of…

The Disguised Dividend for Owner-Employees

The corporation can be viewed from a number of different perspectives. One way is to view it as a group of people coming together to perform some business activity, with each having different relationships and risks in the arrangement. The role any one individual plays in the corporation may not be clearly defined. The owner-employee…