If you are looking at vintage, I can shed some light.
My dad bought a '69 t-top when I was in college. My job was to keep it running and looking good for the car shows.
Very reliable, consisting of few electronics, and the 350 ci with auto trans.
Radio REALLY sucked, but when the engine fired up, you didn't care!
Chassis with the pre-85 models was more like a pickup truck, and the ride quality was just as bad! But you could keep it running with a 1/2" wrench and household items!
Some owners of the early models drove in all sorts of inclement weather, lulled with the rust-free fiberglass bodies, and never paid much attention to the metal underneath, so beware!
Purist cars are the best looking, but not cheap, especially if all the numbers match. Driver cars exist, and can be had for much less money.
Stay away from the fuel injected models and the big blocks if you are looking for bargains.