The old Cherokees are simple and reliable even when abused and neglected. They're also built like tanks. I survived without a scratch after flipping my '96 Cherokee on it's roof and I immediately bought a 2000 Cherokee Sport after that. I had the 2000 for about 7 years or so and even after neglecting to change the oil or keep up on maintenance I never had any serious problems. Looking back though I wish I would have treated it better and held onto it. I regretfully sold it and bought an '03 Ford Ranger(big mistake). Now I'm back to an 05 Grand Cherokee. I'll stick with what I know and love.
I love my jeep. It was the first vehicle I bought from a dealership. It had 90,000 on the clock now it's at near 200,000 I've been everywhere in it. Down in Kentucky all the way to California no issues. Parts are cheap and maintenance is easy. If you have a chance to get one that is really clean, get it.
I bought my 2000 Jeep Cherokee Sport 7 years ago and loved it! It took me everywhere and could do about anything. Ride was a bit rough, but that's a Jeep. Last month I was hit in the rear by an Expedition doing 60 mph. I made it through the accident with only a mild concussion, unfortunately, my Jeep did not make it. It was still going strong with 161,000 miles on it. I miss driving it everyday. I am now out looking for a new Jeep, but only go with used because I want the 4.0L I6 motor!!
I got my Cherokee brand new in 2000, and upgraded to a Wrangler in 2008, 120K miles later. I still have the old Jeep and use it for Home Depot runs and driving in the snow when my wife is using the Wrangler. I beat the heck out of it in the first few years, and honestly didn't maintain it too well. But it's a workhorse; except for brakes, tires, fluids and filters, it still has 100% original parts, has never left me stranded and to this day the engine starts right up on the hottest and coldest days, and the drive train still performs like new. Those I-6 engines have to be the best-built engines around -- I wish they still put them in the Wranglers.
Reliability, solid off-road/snow performance, interior cargo space + roof rack, and it's all-around fun to drive because you just can't break it. Easy to maintain -- I've done all the brake work and fluid changes myself over the years, and everything is accessible and straightforward.
None. It was never sold as a luxury car, a speed machine, a rock crawler, nor a "green" SUV, so it's unreasonable to expect any of those things from it. It's just a solid box on wheels that lets you go where you want, when you want, and doesn't let you down.