My first car was a 1993 Jeep Cherokee. Awesome car that I loved and never have problems until the fuel pumped broke in 2003/2004, and after repairing the same part 5 times without any success, I traded it in for a new Cherokee.
With my 2001 Jeep the transmission seal started wearing away extremely fast, causing a leak. I was told by the dealer mechanics I would have to replace the transmission to fix this, so I just refill the fluid as needed. I tried to have the seal repaired at another auto-shop, but the quick fix they did wore away and I have the same leak.
The crankshaft sensor broke in 2007, and again in 2008. The repairman told me this was an extremely uncommon part to break, so I was surprised when it broke again a second time, but it was less than $200 to repair.
The A/C stopped working around 60/70,000 miles. Another repair to that would be over 1,000 to fix, so I just roll down my windows in the summer.
The power windows work off and on. I can control all windows from the driver's side, however my passengers can only control their windows part of the time when the green light on the button sporadically comes back on.
The key-less entry also works sporadically, as does the right front speaker.
I have had many problems with the car shifting into neutral while idling at a stop light or waiting to turn, then it takes a second for the car to shift back into gear when I push on the accelerator and drive. I don't know if others have had this problem, I still haven't figured out the cause.
A couple of times over the years I have turned on my Jeep and have been unable to get it to go anywhere when I put it in drive or reverse. I try to push on the accelerator and the engine just revs, and I hearing what sounds like a popping noise. After a few minutes of trying, it eventually will kick into gear and reverse, but it's another issue I have not figured out the cause for, and it only happens every once in a while.
I have trouble on the highway at speeds of 45+, the car seems to take an extremely long time to accelerate - I'm not sure if this is a shifting problem in the transmission? The same thing happens in the mountains going up steep hills. My Jeep feels like it's having a really rough time making it up. It didn't have these issues when I got the car in 2004, but after about 2 years or so I started to notice this was happening. Up until now my Jeep has had some unexplained problems, but it's still running.
I would love to keep this car forever, I love the design, but with all the problems I have read from others I wish getting my Jeep up to par wasn't going to feel like a never ending money pit.