https://www.cnbc.com/2020/12/30/bitcoin-nears-27000-why-it-might-make-sense-to-give-some-to-charity.html
You hear that Average Joe? If you have too much Bitcoin, give it away or diversify now!
This is actually a good strategy.
A charitable trust.
If you are able to cash out your gains into a charitable trust you essentially donate the full amount to a charity (executed upon your death).
The trust you put your money into can pay you dividends, pay you from the principle over time, etc.
You know the term "trust fund babies"...you can set up the trust to pay out a certain amount to your children over time, etc.
You get the initial first year benefit of the amount you donated to the charity as a discount on your taxes and you can spread your gains over several years instead of a single lump sum.
I considered this as an option because living overseas I can make up to $100k per year tax free. But I am subject to all taxes on capital gains.
The thing holding me back from doing a charitable trust was that you have to hand your money over to a company unrelated to you to manage the trust. After weighing my options the last time it reached $20k I just could not see putting a lot of money into some fiat based investment that would give me 5-6% yearly gains in a currency losing value at 8-10% per year, run by some idiot fund manager. So I just kept it all in bitcoin and decided to live off of money cashed out at the lowest tax bracket (which is still a lot in 2nd world countries).