I currently own a '95 YJ and the '05 X. One thing that hasn't been mentioned regarding the comparison is the cost of insurance. I pay the same amount for liability ONLY for the Wrangler as I do for full and complete coverage on the X.

Also, I won't let either of my kids drive the Jeep. It is, in my opinion, a very dangerous vehicle for a new driver. You need skill to control that thing under evasive manuevering situtaions. The short wheelbase and no ABS on the Jeep lock the rear wheels almost instantly under hard braking. The insurance is high on that truck for a reason...