Taxes & Tax Planning

You’ve spent decades saving, only to find out that Medicare has a "success penalty." It’s called IRMAA (Income-Related Monthly Adjustment Amount), and it is a cliff. Go one dollar over, and you pay the full surcharge. But there is a defensive move most retirees miss. Tax loss harvesting to...

You worked for 40 years, paid your FICA taxes, and finally retired. You assumed your Social Security check was yours. Then you get your tax bill. Not only is the IRS taking a cut of your benefits, but Medicare just sent a letter saying your premiums are doubling next year. Welcome...

You’ve been generous your whole life. In retirement, you continue to support the charities you care about, writing a check for a few thousand dollars each year. You feel good about it, and you assume your generosity is at least giving you a bit of a break on your...

A Roth conversion ladder can create a rolling source of Roth IRA principal before age 59½. It cannot pay next month's bills. Each taxable conversion has its own five-tax-year period. While you wait, your living expenses, health insurance, and conversion taxes must come from cash, taxable investments, Roth contribution basis,...

The best Roth conversion years before Medicare are not a fixed age range. The safer way to find your Roth conversion “Golden Window” is to count backward from the first calendar year you expect to pay Medicare premiums. Social Security generally uses tax information from two years before the...

A home sale calculator should answer one question before anything else: what is your actual gain? Your mortgage payoff and home equity do not determine taxable gain. The core calculation starts with your amount realized from the sale, subtracts your adjusted cost basis, and then tests whether some or...

A Roth IRA conversion can be a smart tax move when the tax rate you pay on the conversion today is lower than the rate you reasonably expect to face on those dollars later. But the decision is not simply “Roth good, traditional bad.” The amount you convert can...

On January 1, 2021, Tennessee officially eliminated the TN Hall Income Tax, which previously taxed certain investment income. This move positioned Tennessee among the few states without any form of personal income tax, including taxes on capital gains.  Honestly, that's a pretty big deal – a state where you get to keep...

That phone call… it often starts with a mix of grief and a touch of bewilderment. "Michael," they'd say, voice still shaky, "I've just inherited Mom's house in Dallas, TX and honestly beyond the emotions, I'm clueless about what this means financially, especially with taxes. Where do I even...

Most inheritances are not taxable income when you receive them. If you inherit cash, a bank account, stocks, a house, or other property, the value you receive is generally not added to your federal taxable income just because someone left it to you. But that answer changes fast depending on...