This month I've decided to change format. I'm grouping Tax Court thumbnails by category. Not every reader deals with every issue. But coverage is still useful even where only a few specialize. Click here to read the latest happenings!

IRC § 1031 exchanges have the ability to confer substantial financial benefits to taxpayers. Although taxpayers may use § 1031 to place themselves in a superior economic position, taxpayers may not exploit this section in an abusive manner. Taxpayers can use exchanges to give themselves different types of benefits, but one of the primary benefits is the deferral of federal income tax. When conducted correctly, 1031 exchanges are regarded as a form of legitimate tax avoidance. One of the main issues involved with these transactions is determining the boundaries between abusive tax avoidance and non-abusive tax avoidance. In the context of “related party exchanges” – i.e. those transactions which involve subsection 1031(f) – this issue shows up in a relatively complex fashion, because the related party rules are not well understood by most practitioners. Furthermore, determining abusive tax avoidance with related party exchanges is difficult because of the scarcity of case law. Based on the case law which we have, and on the other authoritative references, we can put together a reasonable overview of the risks of related party exchanges. This overview should prove useful when providing expert counsel to taxpayers seeking to conduct this type of transaction. For direct exchanges, the 2-year ownership rule found in 1031(f)(1)(C) should be used as the dominant source of guidance. For “indirect exchanges,” taxpayers must be aware of the higher levels of risk involved, as there is a greater possibility of abusive tax avoidance. To read more click here!

At its peak, Alphonse (Al) Capone’s criminal empire was worth approximately $1.3 billion when adjusted for inflation. On June 5, 1931, Capone was indicted on multiple counts of income tax evasion. At the time the maximum penalty for his offenses was 32 years in jail and $80,000 in fines (almost $1.6M in inflation adjusted dollars). The prosecution in Capone’s case “documented Capone's lavish spending, evidence of a colossal income. The government also submitted proof that Capone was aware of his obligation to pay federal income tax but failed to do so." Click here to keep reading about this fascinating case…

Every tax professional has at least one client that when asked about business mileage replies, “I don’t know; what did I have last year?” You may have read that last sentence and thought, “most of them.” Self-employed taxpayers generally know they must track their mileage, but it’s seldom done correctly, or at all. Vehicle deductions are an area frequently challenged by the IRS on examination as well as an area the taxpayer is unlikely to prevail without strong, contemporaneous documentation. That said, very few taxpayers keep perfect records, so what are the best practices for mileage deductions in the real world? Keep reading to find out!

IRC § 1031 exchanges have the ability to confer substantial financial benefits to taxpayers. Although taxpayers may use § 1031 to place themselves in a superior economic position, taxpayers may not exploit this section in an abusive manner. Taxpayers can use exchanges to give themselves different types of benefits, but one of the primary benefits is the deferral of federal income tax. When conducted correctly, 1031 exchanges are regarded as a form of legitimate tax avoidance. One of the main issues involved with these transactions is determining the boundaries between abusive tax avoidance and non-abusive tax avoidance. In the context of “related party exchanges” – i.e. those transactions which involve subsection 1031(f) – this issue shows up in a relatively complex fashion, because the related party rules are not well understood by most practitioners. Furthermore, determining abusive tax avoidance with related party exchanges is difficult because of the scarcity of case law. Based on the case law which we have, and on the other authoritative references, we can put together a reasonable overview of the risks of related party exchanges. This overview should prove useful when providing expert counsel to taxpayers seeking to conduct this type of transaction. For direct exchanges, the 2-year ownership rule found in 1031(f)(1)(C) should be used as the dominant source of guidance. For “indirect exchanges,” taxpayers must be aware of the higher levels of risk involved, as there is a greater possibility of abusive tax avoidance. To read more click here!

“Timalyn, Alyssa and I filed for divorce, and we will finalize everything before Thanksgiving. Does this change things for our taxes?” “No! Can we wait until January 1?” were my initial thoughts. But then I realized that if this news blindsided me, the seemingly happy couple was probably also scrambling for answers. They were looking to me to be calm during an upcoming storm. To give you some context, I had helped this family lower their back taxes by $16,000 and get a payment plan that worked well with their cash flow. Then, by implementing a few strategies they had just saved an extra $20,000 on their last tax return. We were planning on saving them even more money in upcoming years. Then, that is when it happened. Divorce. I never saw this happening, so I never prepared for it. But if it happened to me, it will happen to you. Clients divorce. Some of the things we are going over today may seem obvious to you. But remember what is obvious to us as tax experts is not obvious to our clients, especially if they are going through a life-changing event such as divorce. Here are four things you need to inform your client about when it comes to their divorce and taxes...

The price of a forever stamp increased from $0.58 to $0.63 on January 1, 2023. A tax pro posted this fact as a public service announcement on Facebook. Of course, tax pros being tax pros, someone chimed in, “Do I have to recognize a capital gain upon disposition of my forever stamp?” And of course, someone (me) felt obliged to answer, “It depends.” A direct message followed this bit of tax drollery on Twitter that says, “In theory, if I’m holding stamps as an investment, they would be a capital asset.” And so it begins…

Reilly’s Fourth Law of Tax: “Execution isn’t everything, but it’s a lot” might be amended when it comes to charitable deduction of property, because there you have an area where execution is almost everything. It is also an area that dramatically illustrates the Seventh Law: “Read the instructions.” In January, we received guidance from the IRS on the reporting requirements for charitable contributions of crypto currency . If you have followed IRS guidance on crypto and know something about charitable donation reporting requirements, the result shouldn’t surprise you , but maybe it will. The most disturbing part of the story is that the IRS may be asking for something we can’t provide...