I probably have ~$25-$28k in my Swinger, and I took every nut and bolt off the car myself. The only work I outsourced was the body work.
I bought the car from Oklahoma thinking it would be near rust free (didn't realize there was such an aggressive snow belt down there). The car was rot-free, but there was enough surface rust in the rear quarters, trunk, and driver's side floorboard to merit necessary repairs/replacement. I paid a guy $4k to do the trunk repairs, repair the existing rear quarters, and get the exterior of the car in primer. I then patched the floors and cleaned up the rest of the car for ~$700-$800 in materials. I then got to pay the paint shop ~$7600 to re-do the shoddy body work and paint the car, and that was a steal from what I've heard. This was a relatively rust-free car sitting in primer when I bought it, and I spent >$12k just in body work (never mind the hood scoop costs and other exterior pieces trim pieces that needed repair).
Unless you're a good body guy (or know one), buy a car that's been restored, then work on the mechanical pieces. There's a reason these guys get paid so much to do the work they do. It takes a lot of time and patience. If you don't have both, I'd recommend buying the car with at least the body work done.
Just my $0.02.
-Mike