Bought a 1986 mazda B2000 for $500, overhauled the brake rotors for another $500 through a shade-tree mechanic. That was 10 years ago and it's still running today. The car was so simple that I made it a personal project/challenge to do all repairs on the car myself. I've done them all over the years except for a new clutch which would have probably been dangerous to do by myself anyway.
The approach I've had was this: Go to a mechanic and have them give me a free estimate for a certain job. They will always give free estimates. Take special note of all the things they say need to be done on the car and the process they would go through to fix it up (Like, I would have never heard of a "valve cover gasket" so I wouldn't have known what to research to fix if I didn't get that keyword from them). If they quoted me $500 for a job, I said: "That's my budget allowed for buying books, parts, and tools to teach myself to do the job on my own." Oftentimes, a $500 job would end up costing around $200. Not only would this get the job done cheaper, I would also 1) learn something new 2) develop a deeper respect and appreciation for that old car and 3) I got to keep all the tools along the way! I've since expanded this approach beyond cars and now into my bikes, and home repair stuff too.