First, keep fixing up the truck. Do NOT go into debt on a vehicle. Pay cash for something you can afford, but that said, take the money you have coming and save/invest most of it. Set yourself up. Or use it for some life experience travel. Don't sink everything you've got into something that will depreciate every day and every mile.
Buy an older jeep. Pay cash. Fix it up but don't put a ton of money into it. You can camp with it, take it to the beach, whatever you want. Chicks will like it because it is outdoorsy and has a convertible/open top. You're not going to be commuting, so you probably don't care that much about mpg.
Resale is usually quick if you don't put a ton of cash into it (as in, don't put monster tires and rims, massive stereo, etc).
If you are an older outdoors guy like me, I'd recommend another pickup truck, but you're still young.
You can go the sportscar route but I'd stick with something with some utility, that's fun, easy to work on/upgrade as needed, and easy/quick to unload if you get shipped out to a locale that forces you to park/store the vehicle.