Personal Finance

If you’re hoping to write off cosmetic surgery on your taxes, the short answer is usually no. The IRS generally treats elective cosmetic procedures as personal expenses, which means they are not deductible as a business expense and usually not deductible as a medical expense either. The normal path to a deduction is documented medical […]

We love animals. Most pet owners do. And if you have ever paid for food, vet visits, grooming, medicine, boarding, or an emergency surgery, you have probably had the same thought at least once: surely some of this should be tax deductible. Usually, it is not. That is the plain tax answer. Most pet expenses […]

Selling appreciated real estate in Virginia can trigger a bigger tax bill than most owners expect. A home sale may qualify for the federal home-sale exclusion, but a rental property, farm, inherited property, or mixed-use property can bring in other issues: Virginia income tax, federal capital gains tax, the 3.8% Net Investment Income Tax, depreciation […]

If you earn strong W-2 income, you’ve probably heard the frustrating rule: rental losses usually can’t offset your salary. For most long-term rentals, that’s true. Short-term rentals are different. Under the right structure, a short-term rental can produce large first-year paper losses that may offset W-2 income or other non-passive income without needing real estate […]

If you run a business as a sole proprietorship, LLC, partnership, or S-Corp, choosing the right retirement plan can materially affect both your tax deduction and how much you can actually save. A SEP IRA is popular mainly because it is easy. That does not mean it is usually the better tax move. In a lot […]

If you’ve ever been hit with an IRS underpayment penalty, you already know how annoying it is. It is one of the most avoidable penalties in the tax code, yet people get tagged with it every year because they misunderstand one basic point: the U.S. tax system is pay-as-you-go. The IRS does not just care […]

If you’re selling investments at a loss and buying them back too quickly, you can accidentally trigger one of the IRS’s most misunderstood rules: the wash sale rule. The stakes are real. A single mistimed trade can wipe out a legitimate tax deduction, push that loss into the future, and create reporting issues that are […]

2021 and all of its tax deadlines are upon us! Below is a quick guide of the most important dates to keep in mind this calendar year. January 15th: due date to pay 4th quarter estimated taxes. February 1st: Due date to send out 1099s and W-2s to recipients. Due date to file 1099-NECs (formerly […]

Longtime readers will remember that I have a more favorable view on debt than most – the right types of debt that is. We’ve written about the dangers of excessive debt, but more often have talked about how the intelligent use of debt can be quite advantageous (examples can be found here, here, and here). […]

2020 and all of its tax deadlines are upon us! Below is a quick guide of the most important dates to keep in mind this calendar year. January 15th: due date to pay 4th quarter estimated taxes. January 31st: Due date to send out 1099s and W-2s to recipients. Due date to file 1099s/1096s with […]

“They used to tell me I was building a dream With peace and glory ahead Why should I be standing in line Just waiting for bread?   Once I built a railroad, I made it run Made it race against time Once I built a railroad, now it’s done Brother, can you spare a dime?” […]

2019 and all of its tax deadlines are upon us! Below is a quick guide of the most important dates to keep in mind this calendar year. January 15th: due date to pay 4th quarter estimated taxes. January 31st: Due date to send out 1099s and W-2s to recipients. Due date to file 1099s/1096s with amounts […]