What would the legal situation be if you want to cash out some BTC that you withdrew from an exchange that is now dead? This im sure it's the case of a lot of people.
Imagine that you sent some BTC to Cryptsy, or any other now dead exchange. You sold your BTC for LTC. LTC then went x4, and you sold it back to BTC. You made a x4 BTC gain, and you withdraw it back to your wallet.
If you tried to sell this BTC to buy a house or something, you couldn't be able to prove your gains due the exchange being dead, and most likely you weren't able to save your trading history because these things happen randomly, exchanges just disappear from nowhere. AND even IF you were able to save your trading history... so what? what proves that you didn't made up your trading history? if the exchange is dead there's no way to verify that your trades and addresses belong to Cryptsy.
Cryptsy went down almost two years ago. None of that trade history should matter for the 2017 tax year (or any future years). The recent IRS comments on like-kind exchanges were just clarification of the existing law. All trading done on Crypsty incurred tax liabilities during the year trades were closed (2013-2016). Typically, a trader would export their trading history at the end of the year for their tax return. It makes sense to regularly export your trading history in case the site disappears (as so many have). As for proving the addresses belonged to Cryptsy, that should be obvious enough from blockchain analysis if anyone really wanted to investigate.
Honestly this is a big mess. This is another reason why im so scared to buy BTC. They could come up with endless reasons to try to steal all of your BTC from you, even if you did nothing wrong. At the minimum opportunity where you can't proven something (such as being unlucky and losing trading history on a dead exchange) they im sure will not make it easy for you, but as worse as possible.
Any thoughts and solutions to this situation?
No exchanges send 1099s (or equivalent tax forms) to their customers at this point. So technically, exported trading history is all anyone (you or the exchange or the IRS) has to go off. Nobody can prove otherwise. As long as your taxes paid appear to have been made in good faith, I wouldn't worry too much.