Jeep Cherokee probably stuck with the 90's models. I have owned three Cherokees, a 92, 94, and a 95 not a single one did I pay more than 2500 for. The 4x4 in a Cherokee is extreemly capable. Gas milage can suck but it will get you where you want to go, then get you home. The 92(Tan one at the top) cost me the most because it was bought from a buy here pay here but it wasn't too bad at the time(it looked a lot different when it was stock
The 94 cost me $300 had a bad low end knock but I just had it for parts, and the 95 at the bottom I bought for $1600 it came with the small lift and 33" BFG's already on it. For the price, the Cherokee is an awesome choice. You can't touch a Wrangler for that price but the Cherokee has the exact same drive train. Only flaw that I could ever find with the Cherokee was the fact that it was uni body and there were some rust issues.
Watch out for rust under the rear cargo area. Common to leak oil around the bottom back of the engine on I6 engines, usually the rear main seal, usually not a big deal but it will leave a quarter size dot every time you park it(it's a bitch to change...trust me). Lift kits and accessories are endless. My vote is Cherokee all the way 1992+ One thing to watch for is the rear end, many come with the Dana 35 rear end, they are not that bad but I would look for one with the Chrysler 8.25 rear end because it is just plain stronger and you can depend on it more.
Here are some pics of all the XJ's I have owned, as you can see they are capable...but they do get stuck when the driver asks too much