I've had a couple of Jeeps...
1. '89 Wrangler (YJ) Islander Package, 4.2 liter, 5-speed. I added a Rancho lift and 32x11.50 BFG AT on 15x10 AR wheels. The only problem that I ever had with it was the little distributor hold-down broke and the timing would wander all over the place! It was loud, rough, and didn't have AC in Scottsdale, AZ.
2. '88 Cherokee Unlimited that I received in exchange for tiling someone's kitchen. It was pretty rough and I put about $5k into it... Tomken 6" lift, slip yoke eliminator, custom drive shaft, 33" BFG MT on black steelies, front winch bumper (don't remember the brand), a bunch of Rusty's Offroad goodies, custom exhaust, all new vacuum lines, and some other stuff. It actually rode pretty well and ended up running great, but it was a pretty uncomfortable vehicle as far as seating position and interior room go. Sold it for $6k.
Definitely not bad experiences with Jeep and they were fun vehicles for me, but I don't think that I'd ever buy one. Why would I? I'm hooked on Toyota now and know too many people with Jeep problems!