Taxes & Tax Planning

You sold inherited property and a Form 1099-S shows a six-figure number in Box 2. It is easy to look at that number and think, “Is all of this taxable?” Usually, no. The 1099-S reports gross proceeds from the sale. Your federal capital gain is generally based on the difference...

Did you know your state could take a bigger bite out of your investment profits than Uncle Sam? State capital gains taxes can significantly impact your bottom line, and the rules vary widely. Many investors are unaware of the complexities of state capital gains taxes, leading to unexpected tax...

"Michael, I just sold my company stock to fund a down payment… my accountant says I owe a fortune in taxes. How is that possible?" This was the panicked call I got from a client, Marcus a few years ago. He sold about $100,000 in stock he’d held for years...

As a financial planner for nearly 30 years, I've helped hundreds of families navigate one of the biggest financial events of their lives: selling their home. The moment the "Sold" sign goes up, the joy is often followed by a wave of anxiety about one thing: taxes. The biggest misconception?...

California has one of the highest combined capital gains tax rates in the country, and it can seriously impact your investment decisions and financial planning. California's capital gains tax system is one of the most aggressive in the U.S., with CA capital gains rates reaching 13.3% for high earners. And worse, no...

If you're trying to figure out how to avoid paying capital gains tax on inherited property, don't start with tax tricks. Start with the gain. In many inheritances, the step-up in basis has already erased most of the appreciation that happened during the previous owner's lifetime. That means the smartest...

A 1031 exchange can defer recognition of gain when you exchange qualifying U.S. real property held for investment or business use for other qualifying like-kind real property. The tax break is real, but the transaction is unforgiving: the property must qualify, you generally cannot take control of the sale...

As a financial advisor for almost 30 years, I’ve had countless clients. Executives from New Jersey, entrepreneurs from California... all move to Florida with the same belief: it's a tax-free paradise. They hear "no income tax" and assume that means every sale is clear of state tax, but they...

For nearly three decades, I’ve had clients walk into my office with a gleam in their eye, uttering the six most dangerous words in financial planning: "I'm moving to a no-income-tax state." Last year, a new client, Robert, did just that. He sold his New York business and bought...

Are financial advisor fees tax deductible in 2026? For most individual investors, no. Personal investment-advisory and financial-planning fees are not deductible on your federal Form 1040 under current law. But the word advisor on an invoice does not settle the tax treatment. A fee tied directly to operating a business,...