I know a lot of guys recommend going for the older models as they have less electronics, but having traction control and such can be awful nice in the winter- especially if you are sharing the vehicle with someone who has less ability to catch a slide or manage wheelspin. The girlfriend has had a few scary moments in my KJ and I really wish it had some electronic nannies. AT tires are pretty bad grip in the cold rain. Combine that with a tall vehicle that has a short wheelbase and you’ve got a vehicle that isn’t inherently stable. Personally if I were to do it again I’d get a Land Rover LR3 for a little bit more cash. The KJ is good in the city though since it is so short, it is very easy to work on and the parts are cheap. Lots of good help here in this forum too. The KJ is definitely an underdog and most people think its a shitbox, so that can be appealing in a way, haha!
I’d look out for gunk in the cooling system as these Jeeps need a particular coolant and lots of people put the wrong stuff in which clogs up the heater core and other stuff. The coolant tank near the fire wall shouldn’t have any coagulated gunk in it. Make sure the heater blows hot! Fixing the heater core is a major PITA.
Common issues are front prop shaft boots failing and taking the U joint with it (easy fix), fan relay failure where the low fan speed doesn’t work anymore (easy fix I’ve heard), and outside of that there isn’t much abnormal issues you wouldn’t see on any other SUV. They wear out ball joints, shocks and tires just like anything else.
Try to find one with the heavy duty cooling pack and skid plates as well. The standard cooling setup is one small electric fan. Look for a big plastic shroud surrounding a clutch fan and you’ll know it has the HD cooling. If you can get a Renegade jump on it! They have the full skid plate package and HD cooling. Getting a set of skids is expensive, so it can save you a lot of cash.
You’ll also notice there was a refresh of the front end in 2005. IMO the early models look better, but you can choose from either front end.
That’s all I can think of for now.