I bought the Cherokee used, knowing it had a couple of small oil leaks.
The day I bought it, the torque converter failed. I negotiated with the wholesale dealer, and he agreed to pay for the repair. However, his mechanic did not do a proper job of replacing the torque converter. Apparently there is a bushing that joins the converter to the crankshaft, and it was the bushing, not so much the converter itself, that was causing the problem. I had a transmission specialist fix this, plus install a new torque converter, and have had no problems since. It was $600, total, for that repair. I also had them install a remote transmission cooler because it is hot here in Texas, and I anticipate doing some towing in the future, and because I feared that the torque converter problem could have put some extra wear and tear on the transmission. The transmission itself is very strong, has never caused any problems. The transmission and converter have been fine for 17,000 miles now.
The oil pressure sending unit (a sensor) failed, apparently because a mechanic bashed it with a wrench while doing an oil change (the sending unit is located directly above the oil filter, so when wrenching the filter off, be careful Jeep owners). It cost me $12 for the new part, and I installed it myself. I now do my own oil changes, so this will not happen again. Note that, with a Jeep, you don't have to put it on a ramp or lift to change the oil! Just roll under there with a pan and drain the oil.
I repaired one of the two oil leaks (see first sentence). The valve cover was leaking, so I got a torque wrench and some RTV sealant, and resealed the valve cover. There are no more leaks from there.
The second oil leak was coming from the oil filter housing. This is a common Jeep 4.0L engine leak. I paid a mechanic ($50) to replace the O-rings ($3 for the O-rings) that are inside the filter housing. The housing no longer leaks.
I'm very impressed with the performance of the Jeep. It is very quick (for a truck, at least), and I've made some modifications to make it a little quicker--larger throttle body, and better exhaust in terms of quality and architecture. I did this to improve low-RPM throttle response, not because I wanted to break speed records.
Above all, I like the fact that the Jeep is simple to repair. I've never found any other vehicle to be so easy to repair at home, so it saves me money over other vehicles. I've found a lot of support in Internet forums (that is how I diagnosed and repaired the oil leaks, and the oil sending unit). I've learned more about vehicles with this machine than I ever expected to. I change all the fluids myself, I adjust things to improve performance, and I've learned what brands of parts I can trust to work. These are things I cannot do on my wife's Buick, nor could I do these things on my old Chevy (my previous car), at least not without special tools or a hydraulic lift.
I chose the 1996 model year because of the reviews on this survey site. I expect the Cherokee's drive train to hold up for many more miles. It seems like, once I fixed the few early problems, nothing else significant is likely to happen.
The ride is stiff, like a sports car, but the steering is not as tight as a sports car. Since it is stiff, it is also bumpy, but bumpy is fun in a Jeep. If it gets to be annoying, I suppose I could replace the shock absorbers or the suspension with more forgiving parts.
The weight distribution in this two-wheel drive model is 52% front, 48% rear (a four-wheel drive model is probably 54/46), so it handles well, but has a high center of gravity because it is an SUV. Nevertheless, it doesn't feel as top-heavy as other SUV's I've test-driven. From what I've read, the Cherokee has a skid-pad maximum of 0.77g, which is quite good for an SUV (a Honda Civic, by way of comparison, has a skid-pad rating of a little over 0.80g). Lower-profile tires would probably improve the handling even more, but that would defeat the purpose of having a vehicle with high ground clearance.
Good-quality tires are important, I learned. The tires that normally come on the Cherokee from the dealership do not stick to the pavement well in rain or snow, though they are fine on dry pavement. I bought new tires, and traction improved dramatically, even though I have only two-wheel drive.
I have taken it off-road. I expected the ride to be even bumpier than on-road, but somehow it wasn't. The Jeep felt at home crawling over large bumps and generally following the shape of the terrain. It wasn't like hitting potholes in the city pavement. It was so much fun that I regret not buying a four-wheel drive Jeep. In fact, I will probably replace my wife's Buick with a four-wheel drive Jeep, soon.
I have leather seats. The driver's seat was worn down a little by the previous owner, whereas all the other seats look like they were never used. So the driver's seat could use some new padding or something, because there's virtually no lumbar support left. Instead of fixing the seat, I bought a special pad that fits over it, which I only use on long-distance trips. The other seats are perfectly comfortable, however, so I assume they were great when new. The driver's seat has power adjustment controls (6-way) that allow a great range of movement. The adjust-ability makes it easy for me to get comfortable during and before a long drive. I understand that people who take their Jeeps off-road don't like to have leather seats because they just suffer damage from the dirt and general hardship of the trails. But for my two-wheel drive city machine, I sure like the leather.
Gas mileage has been consistent at about 17 miles per gallon in city driving, and 20 miles per gallon on the highway. That is expensive, but in my estimation it is worth it for the reliability and fun of owning this Jeep. I get poor gas mileage when my tires are low on air, so I keep a close eye on them. And synthetic motor oil improved gas mileage by almost 1 mile per gallon, on average (I was getting 16.5 miles per gallon before, and now I'm getting 17.3, in average city driving).