I'm a car wh0re. It wouldn't be just one car, I'd buy a whole fleet. Something for every kind of weather/mood.
Old muscle car, probably a Toureg, a small sporty car like a Subaru or Audi, new diesel truck, a REALLY big RV and probably a helicopter to drop it into the places I wanted to camp at(easier than towing).
I'd keep the Jeep though, just cause I built it. Oh yeah I'd get an early '80s AMC Eagle SX/4(the 2 door hatch back), wife had one as her first car and we've always regretted selling it.
So thats if I HAD to spend it on cars. In reality I'd probably buy an acerage for myself and some rental properties. Real Estate is the only thing that seems to hold value these days.