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…
Tax Articles
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…
The “Wait & See” Approach to IRS Tax Debts
While owing money to the IRS is not ideal, it is often manageable. One just needs a view of the longer time horizon. As it turns out, in many cases, the IRS never even bothers to attempt to collect unpaid taxes and/or it ends up only collecting a small amount. While there are a lot…
The Rules of the Game: Burden of Proof in Tax Disputes
Every relationship has rules, whether informal or formal. Every human interaction has them too. One can easily see this in forced relationships. Take organized sports, for example. Organized sports are essentially pre-planned interactions governed by specific rules that all parties agree to follow. The effectiveness of the rules hinges on proper enforcement, which often requires…
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…
The Balancing Act: Records Needed for Tax Positions
The Goldilocks Principle says that the best outcomes are achieved by finding a balance. It looks for the “just right”—neither too much nor too little. This concept applies not only to storytelling but also to tax recordkeeping. Taxpayers have to strike a balance in maintaining records that are thorough enough to satisfy the IRS but…
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…
When the IRS Fails to Timely Respond: Who Pays?
The IRS, like many organizations, faced significant challenges during the COVID-19 pandemic. It had to adapt to new working conditions, which led to delays in processing paperwork, including tax returns, and difficulties in responding to taxpayer inquiries. During this time, when a taxpayer could reach someone at the IRS, they were often told that due…
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…
Allocations After Innocent Spouse Relief Granted
When a married couple files a joint tax return, both spouses are jointly and severally liable for the full amount of tax owed. This means that the IRS can collect the entire tax liability from either spouse, regardless of who earned the income or claimed the deductions. However, in certain situations, a spouse may be…