Sweet plane.
If I had more money than sense, I'd probably get a Columbia 400 so I could carry my family fast, but still land at small airports without, well, dying.
If I had more money than that, I'd get myself a DC-3 with a turboprop conversion and the 'Old Dog' (B-52) treatment.
If I had 'all the money in the world', I'd just pay a crew of people to build me a space infrastructure (along with the mach 25 launchers that would entail). Then I'd hang out at L5 blowing raspberries at you guys before going back to my zero-g sex party.