1991 Oldsmobile Cutlass Supreme
Got the car used in 1996 with 80,000 miles on it. Paid $8k for it, seemed like a good deal at the time, looked and drove clean, was a little lower than blue book value at the time... for the first 4 months, I was quickly falling in love with the car... then everything started to change.
First, the coil housing fried.
Next, the head gasket blew.
Then the O2 sensor died.
Then the timing chain jumped
Then the crankshaft sensor died... the f***ing crankshaft sensor!
That all came over a period of 9 months time, the last 2 coming while on a road trip out of state. After the first, I had to take a f***ing greyhound bus home. Drove back with a friend to pick it up after it was fixed a week later, only to have the last straw happen on the drive home. Drove 2 hours back when the crankshaft sensor went out. Had to leave it with another shop in the middle of nowhere again. That was it...I had it...
A week later, drove down again to pick it up with a friend, got it the rest of the way back home after a 5hr drive, drove straight to a car dealer instead of home, looked at the cars on their lot, test drove a 1994 Ford Probe GT with a stick (had never driven a manual transmission car, so the test drive was hilarious), fell in love with the power of that car and traded in the POS Cutlass for a $2k loss for what I originally paid (never mind the $6k in repairs).
Went from one of the worst car purchases I ever made to one of the best. That Probe? I spent less in total service/ repair dollars over the next 7 years than I paid in 9 months for the Cutlass Supreme.