> If the difference between "realising" your gains annually vs all at once makes a difference for you, it's because you're doing some swimming-with-the-sharks s

> If the difference between "realising" your gains annually vs all at once makes a difference for you, it's because you're doing some swimming-with-the-sharks shenanigans (such as claiming a 100% tax break somehow). Again, how would you handle illiquid assets? It's hard to pay taxes when you can't actually sell a portion of the thing that's being taxed. What, exactly, do you want someone with a house that has appreciated to do? What about someone who worked for an early-stage startup, received some stock that they aren't able to sell yet, but whose 409(a) price has gone up? > I think anyone who retired or bought a house based on the expected profits from their tax-avoidance scheme deserves what they get - sure, it sucks to find out your savings are suddenly worth 5% less than you thought, but if that 5% was because you weren't paying your fair share of taxes, well, tough cookies. Bizarre take. You think everyone who invests and has capital gains did it specifically for the purpose of avoiding taxes?