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Re:We are publishing the tax secrets of the .001% by dakial1 on Tuesday June 08, 2021 @12:12PM (#27437095)
But if the asset sale + the debt leaves you at a loss wouldn't you be able to avoid paying the capital gaibs over the asset sale?
Re:We are publishing the tax secrets of the .001% by cj on Tuesday June 08, 2021 @12:29PM (#27437375)
The theoretical assumes SPY increased over the time period. If it decreased, you could of course sell it and pay 0% since your investment lost money, short/long-term gains wouldn’t matter because there wouldn’t be any gains.

I might be misunderstanding your question though.

Re:We are publishing the tax secrets of the .001% by MR4D on Tuesday June 08, 2021 @12:52PM (#27437666)
Debt is not a loss unless you default on it.