Yes, it’s possible to do much of the basic mechanical work yourself if you have the tools and knowledge, especially on older cars. Bodywork? Not so easy unless Bondo and Rustoleum are your favorite colors. There aren’t many older cars I covet, but I would like to own a 1965 Ford Country Sedan station wagon (without the Country Squire’s tacky fake wood.) Just like the one I grew up with. That my brother and I slept in the back of on vacations. That kind of nostalgia is potent.
I also really like the little, Volvo 1800ES sport wagon of the early seventies. Such a cute, distinctive car. Make mine dark green. Or metallic light blue. Just not the shade of mustard they came in. Yuck.
Step up two decades and get a “better” car for less money. I used to be the (friends proclaimed) king of the $5000-$8000 car. This to me is the sweet spot for extracting the most value out of a used car for the price. Of course, you have to be able to spot the gems and also do your own work. One car I had as a daily driver for about 8 years was a 1989 Camaro RS. Handled like a go-kart but had a decent ride, was pretty good on gas and plenty fast for a daily driver. I never did anything to that car other than routine maintenance and sold it 10 years later for half what I originally paid for it.