Have any US citizens looked into a Charitable Remainder Trust for their BTC? I'm talking to a lawyer next week about setting one up. Seems like the best way to convert capital gains into income. Which, for me living overseas, I would rather have income which is not taxed than gains that are taxed.
Yes. You're basically trading your stash in for an annuity or similar. You can draw a yearly income off of it, but that income itself is still taxable (maybe not so much as an expat?). You're just avoiding cap gains, which might not be as bad as you think. Plus the trust has to be carefully managed to keep the IRS happy.
If you trust in Bitcoin's longevity, you maintain far more control keeping it in Bitcoin, and if Bitcoin cap gains are your only source of income, the first $37.5K are tax free, $75k if you're married, and after that it's only 15%. So say you're married and draw off $150k in pure gains (plus some amount of principle, which might be negligible at this point). The effective tax would only be 7.5%. That's like sale's tax, big f-ing deal.
Gifting Bitcoin also bypasses cap gains. The giftee's cost basis steps up to the date of the gift. Gift every member of your extended family and have them pay for the bulk of your needs. You can gift around $14k per year per person.
The best reason I can see for a charitable remainder trust is if you've totally lost faith in Bitcoin and want to ditch your whole stash pronto for lambos, property, securities, or fiat. Maybe it makes sense to do it for just the part you want to convert, but keep the bulk in Bitcoin until needed. Really depends on your circumstances and faith in Bitcoin.
https://www.estateplanning.com/Understanding-Charitable-Remainder-Trusts/https://www.fool.com/retirement/2016/12/11/long-term-capital-gains-tax-rates-in-2017.aspx