I'd really be happy with just one airplane. I wouldn't want to have to pay for annual inspections, fuel, and maintenance for multiple aircraft. In that case I'd pick this one, a Bowers Fly Baby. I'd get Mark at Stickershock23 to make huge Der Red Max decals for it.
But since this is a fantasy, if I could pick four more aircraft and cost was no object, I'd pick the following:
F4U Corsair. Always been my favorite since I watched Black Sheep Squadron as a kid. I'd upgrade it with an R-2800-CB16 engine If the previous owner hadn't done so already.
P-51 Mustang. I flew this one once and loved it.
C-47. It's a classic, and sometimes I'd want to haul some things around that the smaller planes couldn't carry..
Boeing 707. Another classic, and necessary for trips where you just have to have the speed of a jet and the range. TF33 powered, not J57.
