How do you liquidate bitcoin into dollars without triggering a tax red flag? That was always my concern.
Taxes are taxes. Trying to avoid them will result in a bad time for you.
I doubt there is going to be much “localbitcoin” action when we are talking $10k.
My initial, long term holdings started at about $3,400. I could not cash out today without a parade of tax accountants coming through my life. It is in the deep six figure range. What a problem to have.
For the time being, bookkeeping is horrific unless you buy and hold. Then its an easy capital gain calculation.