If you buy a Jeep for $5000, make sure you have tools.
These things hold heir value well. I spent 8600 on a 99 fixer-upper, 4.0L /auto/soft top.
Be wary of Jeeps that have big lifts, front disconnects, all the bells and whistles: they may have been driven hard off-road. From what I've seen, Jeep people don't sell them simply because they're bored with them.
Happy hunting, and good luck!
If you find one, be sure to post up pics!