heres my opinion on the WJ, its great, although it has its faults. Mine is a stock 2003 stock overland with 100k miles on it. As far as major issues, with it I have had none except for the blend door problem which will plague every WJ eventually. It costs about 200 bucks to fix and can be done by anyone.
The backseat room in my opinion is marginal, but its probably the best of all your options. I have done a 1200mile road trip and spend half of it in the back and I was cramped with another person. We had 4 people in the jeep with ski equipment for 4 and other luggage for 2 weeks, well the entire cargo area was filled top to bottom with stuff on top of the jeep as well. but we managed. the comfort for daily driving these are top notch as far as an off road capable suv.
fuel mileage is better than expected, the overland comes standard with the high output V8. my total combined is usually in the 18-19 range, but depending on terrain and speeds i can reach up to 25 in flat areas doing 55mph. fully loaded doing about 85-90mph we averaged 17.5mpg going from michigan to colorado. normally doing 75mph gets me 21-22mpg as i would drive from ft. campbell to detroit about every other weekend when i was there. the range is good, i can usually get about 370 miles between fillups on trips.
the awd system on it can be great but to clarify what was said, the wj only came with the quadra drive 1 system, the 2 is on late model grand cherokees and is much improved with electronic differentials, but as it is, the quadra drive 1 is amazing... if its working. the system uses viscous coupling limited slip differentials front, rear, and in the transfer case. now, im not sure how the front is biased, but i'm assuming my front is blown out, as im sure all the turning is really hard on the front diff. i was stuck in some snow last month and left the truck in gear and looked out my tires only to find one of the fronts spinning, either than or there wasnt enough speed differential wasnt enough to generate enough heat to lock up the diff. i've also hear of the same problem with the center in some trucks, but mine doesnt have that, at low speeds especially if the transfer case is cold, the rear tires will turn over a few times before it starts locking up the transfer case to send some torque to the front. and the only time i can tell this is when im in deep snow the rear will sink down for a second then all of a sudden massive traction and i drive right out of whatever i was in. in 4LOW though it locks the center diff out completely, and doesnt rely on the viscous coupling. but as this system is, its a MONSTER in the snow and rain tracks perfectly straight even when hydroplaning, or doing 70mph through 8 inches of snow. as far as being weak, i will say its good, the 242hd swap for the transfer case is a good case for even larger tires, the 30 in the front is marginal up to 33s with a soft locker or the quadra drive, and a lot came with d44a which is ok as well. now, for the good stuff, 545rfe is a great transmission, but with all chrysler transmissions it needs to be kept up with fluid changes, it is very strong being found in the 1/2 ram trucks, its a 5spd with a variable lockup torque converter.
off road is good even for being stock, i can manage well on a lot of trails in the turkey bay off road in LBL. the suspension offers good articulation for lots of traction, the biggest down fall is kind of a low ground clearance and have gotten hung up when not carry enough speed.
all in all its comfortable, roomy enough for whoever is sitting in the front, where i feel cramped in xj's, has a great stereo, ice cold air, luxurious enough to take on dates with decent looking wood, and nice leather, capable off road. imo its more less on of the best all round vehicles you could be looking for, i bought my 03 overland with 55k on it in dec '08 for 10.5k so they arent that expensive, im sure if you did you could find a nice one with 100k on it for around 6500 or 7000.
