This is my favourite vehicle! It looks tough, bold, boxy and classic. It has lots of power and the size is perfect. Not too big, not too small and the height gives good sight & overview compared to sedans/coupes. Doesn't feel cramped for both the driver and passengers, but that really depends on your size. You can fit a tonne of stuff especially with the back seats down. They are fairly easy to work on yourself, especially with the help of YouTube and online forums. I haven't used the 4x4 yet, but Cherokees rival the Wranglers when offroading. Now the bad..
It's old. Components are starting to fail and fixing/replacing parts sometimes spawn new problems. Rust is a big problem with this generation of Cherokees, but mine isn't as bad as others (floors and rockers still good). It runs VERY hot. This is apparently normal, but I still believe that all that heat is no good for long term durability/reliability. There are trucks that have a even bigger engine and it still runs cooler than the Cherokees. Fuel mileage is okay, but bad if you're going from a car like a Honda Civic. Right now I'm getting 15.9 MPG or 450-500KM per tank which is average. I can get a little better with proper and regular maintenance.
Cherokees have a Christmas list of common problems, BEWARE. If you love it as much as I do, bite the bullet with the problems and slowly rebuild/restore it as if it were brand new. Just be prepared to dump a lot of money.