Got 3 here. Two of them I don't really use anymore and stay with my dad but they are technically mine and use them very sparingly.
1970 Dodge D-100 - Got it for $50 back in 2002 and only had to put another $50 in it to get the back window replaced and the windshielf wiper motors. Pulled both parts of a pull a part lot. Then had to put another $100 in it to fix up the brake system. Damn thing still runs and can still haul a trailer with a derby car on it. Last time I drove it was around 3 months ago. It rarely gets used. Not good for a work vehicle at all, especially with how much I drive.
1990 Jeep Comanche - Got it for $100 around the same time as the D-100, had to put another $200 in it to fix up the cooling system. Took about 6 months to truly figure out what caused those overheating problems. Damn Mopar replacement parts not exactly matching what was needed. Had to modify the cap on the reservoir to fix it. It has mud tires on the back which causes the ass end to be jacked up a little. Damn thing has some serious pep but eats up the oil more than it should. I haven't driven it in almost a year but my brother uses it every so often. Not good for a work vehicle at all, especially with how much I drive.
2010 Nissan Versa - Got this around 7-8 months ago. This only gets used for work and long trips. Damn good gas mileage. I bought it when my 1996 Ford Contour was on it's last legs. I wanted to get a used car but getting a loan for a used car with little to no credit history was near impossible. It's small, not the prettiest thing around, but I'll be damned if it isn't a smooth ride and much more reliable than that damn Ford.
When I first started driving and even for a while afterwards I wouldn't buy super expensive cars because, well I know how I drive and it isn't good for cars normally. The Nissan Versa is my 14th vehicle since I was 16. I'm 24 now.