Tax Archives

Can a Failed ESOP be Saved by Installment Sale Rules?

Imagine a building with two entrances. Once you’re inside, does it really matter which door you used to enter? This analogy often applies to tax disputes when there are overlapping tax laws. The IRS frequently argues that taxpayers are bound by their initial choice of tax treatment–insisting they stick with the “door” they first entered…

The Short-Term Rental Tax Rules

While short-term rentals have fallen out of favor as of late, they do still offer tax benefits. There are reasons why short-term rentals have more favorable tax treatment than long-term rentals. Short-term rentals often require substantially more active management than traditional long-term leases. Owners must handle frequent turnovers, maintain the property to hotel-like standards, and…

Navigating Late GST Tax Elections: Maximizing Exemptions for Trusts

Those who create or come into significant wealth often face difficult decisions about what to do with it. What is one to do with excess wealth—the wealth that will have no material impact on the owner’s life? The most common solution is to simply do nothing and let the estate tax take about half of…

Strategic S Corp Conversion to Avoid Tax Basis Limitation

Time. We can’t stop it, but we can use it. We can use it to take advantage of compounding to grow our savings. We can use it to pay down debt to increase equity. And we can use it for tax planning. Time is one aspect of tax planning. It can help taxpayers avoid just…

Income Shifting to Reduce Tax for Real Estate Sale

Income shifting is a fundamental income tax planning concept. It involves strategically allocating income among related taxpayers to minimize the overall tax liability. This may be intended to use up tax attributes of one taxpayer (such as deductions or tax credits), take advantage of tax deferral options to delay paying taxes, or take advantage of…

Court Says IRS Can Assess Form 5471 Penalties

Our federal tax system is code-based. This means that most of what the law is can be found in statutes. The premise is that one can read the statutes and get a general idea of what the law is. This is why when it comes to tax law, each word matters. Adding or removing a…

Third-Party Liability for Repaying Employee Retention Credits

Many businesses outsource their human resources to third parties called Professional Employer Organizations (“PEOs”). PEOs are particularly popular with small businesses. The benefits of using a PEO include allowing the business to focus on its business operations rather than HR activities and giving employees access to better employee benefits. This is achieved by having the…

Can a Co-Inheritor Do a 1031 Exchange?

Those who create wealth often accumulate assets to store the value of wealth they create. This includes assets that store value and produce additional income, such as real estate. In many cases, the wealth creator has put considerable time and effort into building their portfolio of investments. But when they die, those who inherit are…

IRS Can Force Business to Use Payroll Service, Court Rules

When a business fails to pay its payroll taxes, the consequences can be severe. The IRS has several collection tools at its disposal to collect unpaid payroll taxes. This includes liens, levies, and even criminal charges against the business owners. The IRS recently attempted to expand its collection powers to prevent future non-compliance. In United…

Tax Form Mixup Can Extend the IRS’s Statute of Limitations

Suppose you file a tax return and, months or years later, you get a letter from the IRS saying that it will not accept the tax return. The IRS letter says that you used the wrong tax form. And maybe even change the facts so that the IRS mailed this letter to you, but you…