1972 VW Dunebuggy
Bought this car for $2400 - actually it was $1800, and with 23% interest on my car loan, it boosted it to $2400 for 2 years - in other words, $100 a month. You know how people brag about how many options their cars have? Well this one had NONE. It had 2 gauges (fuel and speedometer) and 2 switches (headlights and wipers). That's it. No roof, no windows, no doors ... just a big blue plastic tub with a windshield and some 5 point seatbelts.
Had this car for a little over a month, when something blew in the engine. I had to go to work that night, so I left it by the side of the interstate. Came back the next day, and it was gone. No trace. Wasn't impounded, wasn't moved, just ... gone.
The best part of this story is that I didn't have insurance on it, so even though I only drove it for a month and a half, I got to make car payments on it for two years.
Yes, I have learned many lessons the hard way.