If you buy a car that is mostly presentable or one that needs maybe a few things, you could be embarking on a lot of fun for not a lot of money. In addition, some of these classics I’m going to recommend are practical enough to drive to work, run errands and make a decent appearance at your local Cars & Coffee, while appreciating in value.
I especially like presentable cars that are unrestored, and which show just enough patina and careful
use for you not to be afraid to take it anywhere. And the simpler it is mechanically, the more likely for you to develop some repair and maintenance skills on the car which is excellent for further exploration of the hobby.