Tell the rich guy that has seen it all and done it all how much they don't know...yeah, that seems sound.Whatever happens, your outcome will be multiplied.

What was the outcome?

I finished the attic, basement and remodeled interior and exterior What was the outcome?

What was the outcome?

If the house can actually be sold for the $2 million quoted, then I believe the best outcome from a FINANCIAL viewpoint is to sell the property for the $2 million, pay the spouse $550k, pay the $270k mortgage balance, leaving the wife with $1,180,000 cash.  

What was the outcome?

What was the outcome?

What was the outcome?

Updated the decor What was the outcome?

However, this generic statement is useless for many reasons:- your two years are never identical- even if you expect them to be identical, we don't know the future, and things can change- you likely have a number of special factors that change your tax outcome, some of which I mentioned above and others mentioned in earlier comments on this threadWe are also assuming that you're selling outright for cash and not reinvesting, although you have other options such as installment sales (aka owner financing), reinvesting into REITs/DSTs, opportunity zone funds and more, as mentioned in other comments.Finally, nobody brought up what I consider the single most important factor in your decision process: you sell when you have a good offer, period.