Don't know if you are buying as a second, fun car or something you will be driving everyday.
Also do not know if you have any mechanical skills, a decent assort of automotive tools, etc.
Myself, since I value my money, etc, don't like paying for a car that in a month has depreciated 10% to 20%, only one way for a red blooded American, old Marine, to go.
A nicely restored Mustang, Camaro or Challenger to start.
Next would be classic Chevy in the 55 to 58 year range.
There are some others, and if restored correctly and one takes care of them, they just get worth more as time passes.
Plus, anyone with basic mechanical skills can do most repair work on them.
One of my vehicles, actually use it regularly is a 75 Ford Ranchero, 351W, had 72,000 on it, bought i 3 years ago for $2,600 and turn down offers of $4,000+ every month.
I do need to start some metal restoration on it, but drives great, hauls what I need from the lumber yard, my restored small motorcycles, etc.
Am looking at present for a 67/68 Mustang fastback, small block v8, 4 speed perfered.
Grumpy