In my case I think I am doing well with my Mercedes (1992 300TE).
Bought it for 5300$ and 120kmiles with all the records (were about 25k of bills since new, was a Starmark warranty car before).
Completely renewed the whole suspension, drivetrain, exhaust system.
Had minor rust repair done. Did some engine work (tensioner, waterpump, CPS, tune-up). Some interior stuff like new speakers, radio, seat cushion, saftey belt. All fluids, tires etc. Spent about 6000$ (This includes all tools that I own now and all mistakes I did as a complete novice). Drove 35000 miles in 2 years. The car is in better shape now compared to when I bought it and I intend to keep as long as possible.
Friends of mine bought a Honda minivan that has comparable interior space for about 25000$ two years ago (they paid cash). They drove about 5000 miles in these two years. Their insurance is higher than mine (2000 versus 1300 per year). They had no problems except that some anonymous a*** put a big dent while the car was in the parking lot. Would need 2000$ for proper fix. How much would they get if they sell? 10000 or 15000?

Bruno