I bought mine new and put every mile on it. Over 155,000 now and I like it just as much as I did when I bought it. Only needed one repair. Keep the oil changed and kept it clean. Been an excellent vehicle.
As long as you can accept what a Jeep WON'T do, you can truly enjoy what it WILL do. WON'T go over 70 mph WON'T save you money on gas WON'T impress your girlfriend's mother but it WILL go ANYWHERE at about 5 mph WILL save you money up front (it's cheap) WILL look good when dirty This is the coolest vehicle you can obtain for under $5000. Make sure that it's got a manual tranny, 33" tires or larger and a good top. 6-cyl is fast and has a more-reliable transmission but also gulps fuel - but if fuel economy was the point, you'd drive a prius. Get the soundbar, take off the doors and live a little.
Bought my 92 Wrangler used with 33K miles on it. I've driven it over 200K since and she still purrs like a kitten and looks great after a new paint job a few years back. I'm only a shade tree mechanic with a ratchet set and I find it extremely easy to maintain. The inline 4.0, 6 cylinder engine is the best around. Keep the oil clean and it will take care of you. I just replaced the radiator myself with that same old ratchet set. Biggest and easiest repair I've had to make. I confess she is my second car now but she is also my favorite toy to this day. Plan on keeping her forever and giving it to my 2 year old when he is of age. He's already calling it his Jeep.