1988 -> 1983 Ford Escort, blew it up at 49,000 miles
1990 -> 1985 Ford Escort, blew the transmission at 86,000 miles
1993 -> 1992 Geo Storm, bought new in 1993 and sold with 60,000 miles in 1995. A complete waste of money.
1995 -> 1989 Toyota Pickup, wrecked at 139,000 miles. It drove like it had just come off the new car lot. Bought for $6995, 4 wheeled extremely heavily, 2 days before I wrecked, it was completely covered in thick mud. Insurance gave me $8500 for it because of how clean it was (~$1800 over excellent condition book value.)
At this point, I matured and didn't drive the vehicles nearly as hard as I had been.
1996 -> 1994 Toyota 4Runner SR5, Sold at 64,000 miles 6 months later because I couldnt' afford the payment with getting married. Still drove like new.
1996 -> 1988 Toyota 4Runner, my longest ownership. 105-189,000 miles. Never put a dime into it except for brakes and a new clutch. I still heavily 4 wheeled for part of the ownership. Sold in 2002 and I still see it out on the road up north from me.
1998 -> 1996 Nissan Altima, currently 159.000 miles. Still own it. Bought it for the wife after we were married a year. I put a new distributer in it to the tune of $400 since I bought it. That's all I've done except for brake replacement. I took it over from the wife when I bought her a brand new Mazda, see below.
2002 -> 1999 Toyota Tacoma, 91,000 miles and I found the passenger frame rails completely rusted out. Unloaded it to buy the wife a new Mazda so she could have 4wd in the northern Pennsylvania snow. Now a year after I unloaded it, Toyota puts out a recall that they are purchasing back all Tacomas that have the frame rust problem for 1.5 times the excellent condition value. I bought it for $12,500 and after 3 years of driving it, would have recieved $13,800 from Toyota if I still had it.
2007 -> 2006 Mazda Tribute S, currently 15,000 miles. Bought as a leftover / demonstration car with 900 miles on it. $29,900 sticker and fully loaded with everything except leather. Paid $17,900 for it as a brand new car. Suggested retail value currently if bought used at a car dealer is $18,345. Bought mine new a year and a half ago for $445 less than that.