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bitcoin -> Monero -> back to a different bitcoin address. Transparent @rockwellontherun? ;)

Guess the tax authorities will just tell us: «Here is the money you invested as a fact via your broker account. Now you have to show us and prove.» Do you think this is unlikely, Alan?

I would advise NOT using a brokerage account for a start! If you do that, then you could always claim: a). You haven't realised a capital gain & therefore no tax id due, b). You've lost it... i.e sent it to the wrong account.