kytt

Lets play this out from beginning to end. How does someone do this in the real world? Step by step.

My biggest fear would be liquidation. Are you trading BTC for Tether is say a Exodus wallet than cashing it out on Coinbase? After that take USD to bank? There is still a paper trail 

I guess my question is, when you need USD how do you actually get it without putting yourself at risk? I've never seen any content on how this could actually be done step by step. Would love to see it though, for educational purposes only, obviously ;) 

Maybe one day I'll be 100% BTC. I'd like that day to come, but I'm willing to sacrifice the potential gain for a bit less developer/miner confrontation, and much less regulatory attacks.
I'm not sure flipping it all into no-kyc Bitcoin would go very smoothly. Like OP is saying, you still have to move the dollars through banking system and questionable transactions with an anonymous willing party. 

Eobard

Suggestions on avoiding capital gains tax definitely welcome....
 
Wife and i own house outright. No kids. Remaining liquid assets at current market value are 50% BTC and 50% traditional investments. Age, mid 40's. Very VERY small income, but don't really NEED to work from a financial point of view.

At the moment our plan is just to live in smaller income brackets to keep tax bill low. But, I mean, if BTC does what we all hope it does in next 20 years there might some rather painful capital gains. Or maybe we can live in BTC denominated economy in 20 years, but that seems a stretch.