Truck. Trust us older drivers when we say that it's worth it. Less worry about scratches, and with a full size pickup, that dent will just fit in with the others.
Best advice: K1500 Silverado or Sierra. Extended Cab with short box/stepside bed. V8, 4x4, cheap, and tons of fun.
Effin' bulletproof. Not to mention it's no big deal to crank 300K miles in one because it will keep going until the frame rusts out. IMO I'd stick with a 90s truck, because if you start getting back into 1987 or older the more expensive it will run you to find a good running example, since it will be someone's mud truck modded up the wazoo, or a pristine show truck.