I bought a 1999 grand cherokee 4.0L last summer for my job. I needed more room to haul parts and equipment. Its one of the nicest things I've ever driven. I spend 60-70% of my day in it (so much that I even have a laptop mount just to give you an idea) and I'll say its very comfortable. `99-04's still have solid axles in the front and rear so they do still ride a bit like a truck, but jeep did an excellent job of making that easy to deal with and I doubt mines ever had shocks (142,000miles) now.
I got it because the engine/driveline is very reliable and its very easy to work on and cheap to get parts. Down side is gas mileage being in the 17-21 range, but thats comparable to any 4x4 vehicle including small things such as Chevy Trackers and toyota pickups.
I paid $3800 for mine and so far its been very good. Just small maint items that I noticed it needed. As for the comments a few replys ago about rattle trap this one I bought is great and I pull U-turns off the pavement all the time, hit or jump curbs, drive long distance in construction sites (we do a lot of work with kokosing) and I've never hear a rattle or had a dome light flash on (some do this.)
Also you gotta appreciate that the vehicles original buyer was well into the middle class, the vehicle was high price tag for the SUV market of the times and it is a flag ship vehicle for Jeep Corp and you get them used very cheap now.