Last May, we bought our "new" car -- a 1994 Isuzu Rodeo. Yeah, it was 20 years old and would obviously need TLC to be kept in good operating condition, but our calculation ran like this:
If it lasted six months without requiring major repairs, it would be a better deal than putting the same amount of money ($1500) down and making financing payments of $200-300 per month plus higher insurance rates (full coverage instead of just liability) for a new or nearly-new vehicle. And if it didn't make it that long, well, roll the dice again -- it will average out.
Nine months later, the thing is still running (meaning it has more than "paid for itself" per the calculation above), but it's at the point of really needing some of that TLC. The power windows aren't working. The problem seems to be a weird relay (instead of a regular fuse) that AutoZone can't find in its parts catalogs, meaning I can't do this myself, and it would be a minimum $100-$200 to get them fixed (because the shop would want to do electrical tests, etc. instead of just plugging in a new relay). It will need new -- big, expensive, SUV-size -- tires soon. The oil pressure runs low, which probably means the engine is nearing the end of its life (no surprise -- it's got about 250,000 miles on it), and so forth.
By way of preparedness, Tamara started watching Craigslist for a good deal several months ago. She pulled the trigger this weekend: $1350 for an even older vehicle with only slightly less mileage. But this one is a 1989 Volvo sedan that's obviously and visibly been well cared for. Same owner for the last 17 years. It served as first car for two high school kids, then became a "spare daily driver." The couple recently decided that two cars were enough and priced it slightly below "blue book" value.
I expect this one to serve us well for far longer than six months. And we're already ahead of the "pays for itself" curve. But mostly I'm happy to see Tamara in a Volvo. Kind of expensive to repair when they break down, but they don't break down very often and they usually top the lists of cars that protect passengers well in accident situations. And they're comfortable.