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 have owned this 2000 classic for 16 years. Tires and fluids are all it has needed and 1 power steering pump. 144000 miles of trouble free on and off road use. Carries more than an Wrangler and can go the same places. Mileage averages 17 MPG on regular gas. Winch, 3 inch lift, Rear axle locker, Took it to off road at Telico, NC. no issues if you know how to drive. Best vehicle I have ever owned and I have had many over the years. Still it's my daily driver.
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.