My quick reply...
The XJ for reliability, and I've had 4 XJ's, three ZJ's and one MJ.
My best cherokee with loads of money spent, really before they were popular to lift. 7"es of lift on 35's
and a whole lot of other parts. Great on the road and off.
The XJ auto is an Aisin 4 speed auto from Japan. Similar unit used in the toyota pickups. Bulletproof tranny. The I-6 is incredible, lots of power and good to
5000lbs of hauling with weight distribution hitch. You can get a ZJ GC with the I-6 and the Aisin Tranny too, but too many other problems with the GC.
1999 IMOP is the best year for the XJ. last year before distributor less , 8.25 29 spline rear end, less restricted I-6.
Watch for rust, as the XJ, ZJ, WJ are unibody construction.
242 is a great transfer case, stronger than the 231, and not too hard to find. Look at the limiteds for best chance of having one.
The only problem with the XJ? The rear seat is awful!!!!! I changed out the rear seat in my last XJ with a rear seat out of a ZJ. Can be done with minor trimming.
The WJ and ZJ have more problems with the basic mechanicals, and if you get the V-8 in the ZJ it's a three speed auto and full-time all-wheel-drive. the viscous
coupler is notorius failure. A 242 or 231 are easy swaps though. Power windows often fail in the ZJ, and WJ as well as the HVAC blend doors. The V-8 ZJ's do have a rear
dana 44 but it's aluminum and limited with options for gearing.
A big problem with all these year cherokees are the fuel tanks hang low and behind the rear axle. Not good for rear end collisions. Steel plate gas tank skid plates are
readily available though.
The only Grand Cherokee I really love is the illusive 5.9L That thing is absolutely incredible. I dropped a 231 in it, 33's on 4 inch lift, adj' arms, SYE, and body protection.
Not my 5.9L but very similar to what mine looked like before the wreck
This was 3" OME with 38" SS, just a test fit from my MJ
Wheeling with all the cherokees, the XJ is more nimble, and makes a great offroader with their coil sprung front end and the leaf sprung rear.
If you lift over 3"es plan on long arms or drop brackets with adjustable control arms. For the GC you will need adjustable control arms for the rear as well as they are coil sprung.
The absolute best family expedition vehicle is the... I know this is sacrilegious on this Jeep part of the forum, the FJ80 hands down. (and believe me, I love Jeeps) The 80's are getting cheaper
to purchase now, three rows of seating, all wheel drive. throw a 3" OME suspension on there, and drop the 4:10 gearing to 5:13 with 33's and your good.
The least amount I spent on any off road vehicle thanks to a good friend of mine in the know. ($3500 bucks with purchase price)
all leaf sprung MJ on grand wag 44's 5:13's and 38" SS shortened LB with spool in the rear and lock-rite in front.