I have a ton of bitcoins from about '09 that I've decided I want to start selling them off. The problem is, over the years, they have been moved around a lot. Different exchanges, back and forth between exchange-money and bitcoins, many times, but I've never put them into my own bank account. I mean maybe a few here and there, but whose counting. The problem is this, most if not all of the exchanges I ever used are gone. Shut down. Inaccessible. It also goes without saying that these are certainly not the same coins I had years ago.
I was thinking of just selling them off over time, declaring that transaction that makes it to my bank as capital gains, paying the tax, and being done with it. I don't see any way I can get history of all those micro transfers over the years. I've talked to tax lawyers, they haven't a clue on anything about bitcoin. They told me to just treat it as the single sale of a commodity (each bank withdrawal), pay tax on the capital gain, and be done with it.
Thoughts? Suggestions? I want to reiterate the sheer amount of bitcoins I have. Selling them all at once would absolutely crash the market, which I do not want, and the amount is certainly high enough to potentially warrant an audit, so I want to prepare for that. I don't plan to take any deductions so I don't think the audit risk is too high. I have no objections to paying taxes and want to make sure I do it correctly.
That is a VERY difficult topic i had to deal with too.
Lawyers have no clue, right. Though you might meet lawyers that are specialized in bitcoin. Every country should have such. Ask the exchanges in your country which lawyers they use.
Then... the problem is you can't proof anything. Of course you can claim profits, the IRS will happily take your money for that but you can't proof your expenses. And the thing is, you need to proof expenses and the IRS need to proof you had income.
So i think be cautious and maybe do as you thought to do. Though you should be able to explain where the money comes from. If you explain you won it by trading on an exchange that is gone and you only have your notes anymore then that is what they will accept.
I know this is a VERY fearsome topic. But in your situation you can't go back or forth really.
Good luck with that.