wranglers don't depreciate a whole lot, at least not to this point. my advice would be this:
if you're planning to do a lift and new tires and bumpers...you're basically talking about capability modifications. and, you mentioned off-roading. i think you really would rather have a wrangler but are concerned about money. all i can say is that when i really wanted a pick up truck, i bought a large SUV instead because i found a good deal on it and it was nice, but it was not long that i was regretting that decision and got rid of it inside a year for a truck. i was poorer but happier. if you can swing it financially, buy what you really want and be happy. check into tj wranglers. i know i sound biased, but they are solid vehicles and you'll get more to your price range. i bet you could pick up an 05 or 06 for around 15K with not tons of miles.
2003 Rubicon (shale green/khaki), 33x12.5x15 BFG Mud KM2s on Pro Comp 8179s (Firestone Winterforce on stock Moabs for winter), Bilstein 5100s, 3" AEV (nth) Progessive coils, OME steering stabilizer, 1" M.O.R.E. body lift, JKS adj. track bar in the front, 1" JKS budget motor mount lift, RC quick discos, OR-Fab rear rock crawler bumper with 2" receiver, Rokmen 3/16" steering box skid plate, Rokmen rear frame tie-ins, Teraflex 3/16" heavy-duty oil pan skid plate, Alpine CDE-124SXM CD/sat radio MP3 player, Bestop sliding windows, Bestop Safari Bikini top (green military camo), Mopar "windjammer" rear window, Mopar "duster" tonneau cover with tailgate bar, Rockhard Full roll cage with full padding, KC slimlites long range/off road lights on KC windshield mounts, Tuffy security glove box, Pilot LED tail lights.