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Yes, you’ve got the “sticker price” of the collectible tax right. But with an $800,000 MAGI and a $100,000 gain, there are three hidden tax impacts this year that didn’t apply when you were in the 12% bracket.   You mentioned a $100,000 profit. Collectibles (Art, Antiques, and specialized "Collectible Cars") are taxed at a maximum rate of 28%.  Because you are in the 37% ordinary bracket, your collectible gain will be taxed at the 28% cap.   The hidden impact of this is that collectible gains are "stacked" on top of your ordinary income. While the gain itself is capped at 28%, it pushes every other dollar of your "regular" Long term Captial Gains (LTCG)  (if you had any) into the 20% bracket. Since you said you have no other passive income/LTCG, this won't hurt you directly, but it effectively uses up your lower tax rungs of the LTC.   You mentioned you don’t have “other” passive income, but the $100,000 gain from the car is considered Net Investment Income.   Threshold: For married couples filing jointly, the Net Investment Income Tax (NIIT) applies once your MAGI goes over $250,000. Impact: With your MAGI at $800,000 from the Roth conversions, the full $100,000 gain will be subject to an extra 3.8% tax. Total Tax Rate: Your effective federal tax rate on that car is 31.8% (28% plus 3.8%), not just 28%. Even though you aren't on Medicare for 3 more years, your 2026 income is the "Look-back" year for your 2028 premiums.If you are on Medicare in 2028, the Social Security Administration will look at your 2026 Tax Return. With an $800k MAGI + $100k gain ($900k total), you will hit the highest tier of IRMAA. For a couple, this can add up to $12,000 to $15,000 per year in surcharges for Part B and Part D.   Since you plan to start Medicare in 2029, the increase in 2026 may no longer affect you by then. If you sell in 2027, though, that could raise your 2029 premiums. Selling in 2026 is a safer option for Medicare if you’re starting coverage in 2029.   @howjltx