I have had no problems with my jeep yet besides the regular maintenance like brakes and tires.
Both front right and left fenders have fallen off going highway speeds, which was a pain in the butt to have to put them back on again after they got re-painted. I highly suggest using PB Blaster on the bracket bolts.
I replaced both the leaf springs because they were sagging a lot and looked really bad. total labor time was 6 hours and about $200 bucks to do and a lot of PB- Blaster on the bolts.
When I first got my jeep I was planning on lifting it, but as I started researching it I found out that it was going to be quite costly, althought I will do it one of these days. So I decided to go the other route, making it quicker. So far all I have done is add a cold air intake with a K&N air filter. The Jeep really hauls, off the line and has good all around power. Future mods will be a bored throttle body and a cat-back exhaust. I have taken it off the road quite a few times and have never gotten stuck, except in a huge snow drift I tried to plow through. I love the 4 wheel drive system. very easy to use and feels very powerful and capable, I really like 4Hi becaue you can use it whenever even on dry pavement at highway speeds with out damaging the transfer case. The interior is OK. It is a little tight in the back seats. The front seats seem to be decent, although I have only done a few 200 mile trips. the trunk space is a good size. The Classic can look very good when cleaned/waxed and with all the nessesary detailing stuff. Well hopes this helps. keep in mind that the Cherokee has a very potential engine and can be a very capable off-roader also.