This is my first Jeep and I wouldn't hesitate to purchase another one. The 4.0L is a torque monster that pulls better than any other compact SUV I've ever driven. The Command-Trac 4wd system works flawlessly and allows this Jeep to go almost anywhere. Snow isn't a problem, just point where you want to go and hit the gas. I'm 6'4" and drive in a very upright position and I've got enough headroom so that I'm not ducking while I drive. As far as brakes go I personally haven't had any problems with them at all. There are a couple of real minor flaws inside. The transfer case lever does vibrate as does the exhaust system but these are minor flaws. Overall the Cherokee is a real SUV not a cute-ute.
Torque monster. 4.0L. Excellent on and off road ability. Solid front and rear axles. An excellent comprimise between overall size and cargo space. Awe inspiring four wheel drive ability. Tons of aftermarket accesories. Lots of Jeep clubs
No longer made. As for used ones there are tons of aftermarket parts out there for 'em.