For me personally, I need some sort of utility vehicle which is used for work and pleasure.
My choice was made 4 years ago when an absolutely superb 92 jeep cherokee came my way.
It had 150k very well maintained mechanic owned miles on it.
Seems the daughter went out for a drive on the highway blasting the radio and never looking down at the gages. That is untill it started spewing anti freeze and steam all up on the windshield.
Ling story short, it ended up parked next to my shop. After inquiring about it, I was told it needed a new water pump (original issue that caused coolant to leak and over heat the engine) which then caused the head to slightly warp, which also resulted in some hailine cracks.
So. I talked him into letting me have it for 800. I put another 400 into a used/ rebuilt head, entire new cooling system. Just to be on the safe side. Total investment was 1200. It only get 18-22 mpg's, but for as little as I paid for it, and the use it gets doing daily commuting, picking up car parts, and weekend excursions out in the Arizona Desert (natures unplugged entertainment), I feel I made the right choice. Maintenance so far has been front brakes, 35., crank position sensor 52., fuel pressure regulator 65. Not bad for a vehicle now reaching 245k miles :)
It think it earns a mustachian award :)