I was thinking of this after watching @dollarvigilante and here are some of my thoughts on the future of BTC and Urinal Sam.
I believe the government will treat BTC like any exchanged commodity or stock. They won't/can't tax you while it is being exchanged and the price is fluctuating (after all thats exactly what stocks, commodities, and forex are doing). And while the BTC is "trading" you have not fully exchanged goods for a profit/loss. But the second you turn that to liquidable cash assets, they will tax you. Of course bc they want their significant share.
So my theory is, if you want to "clean" your BTC in exchange for cold hard untraced cash, buy silver or gold online or dealer who accepts BTC (easy to find in NYC if you live here). You have your metals in hand, and then you just turn it back over for cash. I could be wrong, but this seems like a work around as you're exchanging an exchange for a product the government has no idea how much you're purchasing or how much you own.