The transmission sensor went out, then the ignition broke, preventing the key from turning.
The radiator came apart and flooded the transmission with coolant (as the coolant passes through the radiator).
The Electric window just fell down the door, and the electric locks stopped working right before I had to go on a trip, so I would lock the tailgate with an "S" hook and a piece of rope.
The door covers both kept popping out until I drilled holes in them, and added sheet metal screws. The brakes were also a big problem.
I bought the extended warranty which doesn't pay for crap. My synopsis of a Jeep extended service plan is this. "If you are driving down the road and the engine falls out of your Jeep, Jeep will replace the motor mounts free of charge. Of course you will have to pay the $72.00 per hour for one of their incompetent mechanics to install them. That is if you were stupid (like me) and bought their extended service (rip off) plan. I have had two Jeeps - My first and my last, both the same vehicle.
This car would have been better as an artificial reef.
My 1999 is troublefree. Since I know they are prone to seal failure (TC, diff yoke) I just keep an eye on it. It runs solid and drive like new. OBD II tells me the rest.