Somebody was going to do "mile high club" flights recently; not sure how far they got. They would need an AOC for A-A charter which is about 20k up front and then 5k/year.
Gives a whole new meaning to "pleasure flights".
I wouldn't worry about the wind corrections. That is one thing you do in flight. The forecast winds are often bollox anyway, so any wind correction will be out by 2x anyway...
In reality you fly with a GPS and the wind aloft becomes almost immaterial, except in its effect on your range.