The WJ is comfy, but if you want simple and reliable, get a ZJ instead (93 - 98, the 96 - 98 facelifted ones are the best of the bunch). It'll be just as cheap (if not even cheaper), they're simpler, only a little worse riding (still pretty comfy for having stick axles at both ends) and they've got better engine options IMO. WJs are a little bigger inside though (and have better cargo space due to the spare tire being under the floor instead of in the cargo area).
In a WJ, you'd want the V8. Just don't let it overheat. Ever. You'll likely cost yourself a set of heads (or a dropped valve seat and a whole motor) if you do. The 4.0 I6 of those years tends to crack heads randomly for no reason at all, even if never overheated (and the cracks dump coolant straight into the oil, not into the cylinders). Transmission behind the 4.0 is a hair on the weak side, the one behind the 4.7 (V8) is much better.
If you look at a ZJ, you also want a V8. Just as reliable as the 4.0 of those years (if not more so) as long as the intake plenum gasket gets fixed. The V8 ZJs have the most potential power upgrades of the bunch if you get bored. V8 ZJ transmissions are pretty beefy, especially if you upgrade the cooling and do the occasional band adjustment and fluid change. A few turns on the line pressure screw helps too (and makes them shift a lot nicer). The 93 - 95 5.2s and 98 5.9s have the beefiest transmissions of the group (46RH and 46RE compared to the 44RE the 96 - 98 5.2s use).
In either Jeep the 4.0 doesn't save a whole lot of gas, so it's not worth the lack of power and smaller trans IMO. Gas mileage between the ZJ and WJ is pretty close as well, slight edge to the WJ there. That difference probably drops to 0 when towing. Cruising range is pretty similar, as the ZJ fuel tank is bigger (23 gal vs 20.5 for the WJ).
In either case, they're not overly big or long wheelbase (105.9" for both), so I'd tend to stay away from lifting it if you're towing with it. With either one, 30 - 31" tires will fit at stock height if you don't go too wide. If you don't mind doing a little trimming, you should be able to get a skinny 32" (like a 235/85R16) under there. WJs have a hair more tire clearance IIRC (especially to the front lower control arms), but it's not a big difference.
For 4wd systems, in the WJ, V8s will usually (but not always) come with one of the fulltime systems. Quadra-Drive is the most capable of those (heavily rear biased until slip in high range, locked center in low range, limited slips in both axles). In a ZJ, V8s always have the fulltime system. Those ones will have viscous coupler issues (binding in tight turns) eventually, but swapping the case to a rebuilt one or a part time unit is easy. Some ZJs have limited slips in the rear, some don't. 96 - 98 V8 ZJs, all V8 WJs and 4.0 WJs with Quadra-Drive have the bigger D44a rear axle (3.73), the rest have the smaller D35 (3.73 for 93 - 95 ZJ V8 and any 4.0 with tow package, 3.55 for 4.0 without tow package). All have low pinion D30 front axles.
IMO, ZJs feel a little better on the road. A little more of the feel of driving an old muscle car in terms of how it responds and power delivery. WJs are a little more responsive in the steering, but also more cloud-like and disconnected in other ways.
Both have pretty simple suspension for any modding you may want to do that's near stock height. ZJ suspension layout is a little simpler / easier to work with (both are a 4 link + panhard up front, ZJ is the same in the rear, WJ rear is a 3-ish link with an upper A arm and no panhard). IMO, the ZJ rear suspension is a little more stable / planted feeling for towing. WJ track width is a hair wider (59.5" at both ends vs 58.5 front and 58.8 rear for the ZJ). That's easily fixable with wheel spacers if you care about the difference for towing stability.
