jbreher
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October 26, 2017, 08:38:30 PM

Although you guys can do what you want, I would really encourage you to think differently. First, selling even a half million $$ worth of bitcoin would incur a HUGE tax penalty right off the top. You took all the risk with your own money, so why would you give your tax agency 40% of all of your gains?

Hmm. Long term cap gains 'round these parts is more like half of that figure. I'm considering wintering in Puerto Rico in the future - 183 days qualifies for citizenship, and LT cap gains there are a drop in the bucket. They get a special US Legislative deferment on federal cap gains.

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Holding bitcoin long term will beat the snot out of future inflation.

Such is my belief as well.

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Personally for me there is no "exit strategy", I will continue to buy and hold as long as Bitcoin is around, and only spend what I need to live day-to-day, month-to-month, etc.

That is my plan as well, though for me, the accumulation phase is essentially done and dusted. When I am ready for more fiat, I trade the volatility for a bit (as described upthread). I can usually come out of it with the same or more Bitcoin, and the fiat I need.

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And if you want to own a house or land, it would be smarter to only liquidate enough bitcoin for a sizable down payment, and then get a really good low fixed rate 30yr loan for the rest. Bitcoin's yearly returns would handily beat, actually crush any 3-4% yearly interest on the loan. Plus both the house/land AND your left over bitcoin would both be increasing in value relative to fiat while you were still making loan payments.

I've done that for 35 acres of paradise this year.