I really think a key factor is whether the prospective owner is mechanically inclined, has/can done/do a lot of basic work...and some diagnosis, etc. My impression is that Eric fits that mold.
Our son is really a good shade tree mechanic. He's mid-thirties, and he's assembled a great set of tools. His first car was one that would but anybody in the poor house, had they just "taken it to the dealer" for diagnosis, let alone work. You run up a LOT of bills, at $150/hr. for labor, versus being able to do the work....and source the parts yourself.
Recently he replaced a oil pan gasket, which the BMW service network "books" as, I think a 12 hour job. Maybe 18? It's astoundingly expensive. The gasket costs less that $100. He can do that kind of work.....which involved dropping a subframe member to get the pan dropped. Replace a starter, an alternator, timing belts, pumps.....nothing. Brake work? piece of cake.
That second car was a 1995.5 Audi S6 Avant, with a six speed conversion, bigger manifolds, bigger turbos, Stromong exhaust. He did all of the work on it. Finally decided that finding places to work on it.....like renting a garage space on a Sunday, was a pain in the neck and he went practical. A Tacoma that I bet will run to 5-600K miles.
The ability to do a lot of work yourself, and to get to know your car, drastically lowers the cost of ownership and increases your familiarity with the car.
Owing an older one, and one that's pretty sophisticated. Not wise. A neighbor recently bought his 17 year old son a older BMW 750i. "OMG, it was a $100K car and I bought it for $8500!" This guy, let alone the son, does not have a single mechanical bone in his body. Not a one. Good surgeon, I guess. That thing is going to be a disaster. They are used to "BWM Dealership Service." We have two great independent BMW techs nearby...... 30 to 45 minutes....and having them do work involves the usual timing and such that you get with an indie. I spoke with an older friend who has an original 740i short wheel base {before they got too exotic with too many microprocessors, he says}. He jokes that when the new ones start throwing codes, it's like the Fourth of July on the dash. And his work was that the 750i new to the neighborhood has something north of 50 in it. It will be one thing to have it at home. I can't even imagine that thing going away to college with the son and living outside. Disaster in the making!
I would not even consider many cars unless you have a good code reader and can pull codes, and can do 95% of the routine maintenance yourself. You need space and time. Helps if you enjoy it, too. And it's a lot better with a rust free vehicle...speaking from experience, HaHa.
Another factor is how far away from home you might drive it. Has never bothered me, and I travel with key spares and tools. I've driven 250K+ vehicles 2000+ miles at once. However, it puts some people on edge. Which I completely understand.
Just my $.02.
