Skydiving planes are cheap compared to some planes. In fact a used diver driver is probably on the cheaper end of used certified aircraft since they are modified for the purpose and have little use to regular pilots as anything but a jump plane, and getting a Cessna 185 that isn’t beat to fuck and then modifying it so that they can then beat it to fuck, is probably a better investment for a jump school long-term.
Wanting to fly warbirds, that’s some privileged-ass territory. Need millions of dollars to buy and restore a fighter that was mass produced to last weeks, that is now getting close to 80 years old, to flying condition; and then probably something close to $1000 an hour in costs to actually fly it, by the time you add up the dozens of gallons per hour of fuel plus the maintenance plus the yearly salaries of the mechanics. And I probably am not including the taxes and fees and insurance.
It’s about on par with yachting I suppose since those are not cheap boats and you need to hire crews and all.
But you can do a lot with a yacht. Host evil villain meetings, hold arms deals with some rebel faction, shoot music videos, etc. The most you can do with a warbird is go really fast, really loudly, and try not to kill yourself while destroying a piece of history.
If we want to keep climbing the pile tho, there’s the Reno Air Race teams who take those same warbirds and then spend many years hot-rodding them into the fastest non-jet aircraft to have ever flown, and then proceed to race the things out in the desert to win… I don’t even know. The attention of the other folks who are in that sport I guess.