1996 Subaru Outback. Most of the issues I had were previous owner related, or partially my fault. This was back in 2011, when I was less mechanically inclined, which didn't help.
I drove all the way down to West Virginia (I think?) to buy it because I really wanted a blue one. I had sent a money order to hold it, and when I got there the guy could tell it wasn't in as good of condition as I thought it would be, and offered to give me back the hold money and let me walk away, but I ended up buying it.
None of the 12v outlets worked, so my GPS died on the way home and I ended up driving almost an hour in the wrong direction somehow. It was also burning/leaking some fluid, but I couldn't identify what it was on the way home since the oil and transmission fluid seemed to be fine (except somehow I mistook the diff fluid level for oil, so I was never checking the oil). When I was almost home, the oil pressure light started flickering at idle, so THEN I realized what fluid was causing the smoke every time I would shut the car off.
Before I fixed any of the issues it had, I swapped in heated front seats, deep cleaned the whole car, installed new head lights and an aftermarket stereo. This would of course become a waste of time and money.
It had torque bind, and after draining the trans fluid and finding WAY too much in there (filled an 8 quart drain pan completely and then some), and that the diff was ALSO full of trans fluid, I ended up replacing the transmission. Unfortunately I wasn't confident in my ability to do the swap myself, since it was AWD, so I took it to the cheapest shop I could find, that replaced the transmission but ignored any other issues they found along the way, and then had to shorten the exhaust to get it to fit, which made no sense at all. It also wouldn't idle once it was warmed up, since they forgot to plug in the IAC sensor.
Got it home and realized that while the torque bind is gone, the massive oil leak still exists, and diagnosed that it was the oil separator plate, which is of course on the back of the engine, and the transmission has to come out again. Couldn't afford to have a shop do it, so I did it with help from my dad. Replaced the separator plate gasket (or used RTV, whatever the correct thing was), and put it back together. Changed the oil and went for a test drive.
Less than 15 minutes later, the car died coming up to a light. It started back up, but didn't sound right. ROD KNOCK.
I gave up on that car at that moment, parked it and walked home. Went and got it later and sold it for nowhere near what I paid for it, and the parts and labor, but it was enough to buy a 1991 Escort, which went on to be one of the most reliable cars I've owned.
Oddly enough, all my other Subaru experiences have been good. 3 Saabarus, combined 80,000 miles with no huge repairs. Worse was an alternator. Granted, at 260,000 miles one developed an external head gasket leak, but the others succeeded at containing their coolant.