What's more reliable? Forester or cherokee?

Can't comment on the Subaru but have owned Jeeps on and off my whole life. Currently own a '96 and '00 Cherokee Sports. Jeeps are easier to work on and parts are not expensive. My '96 I paid $300 for with 151K. Structurally the thing is a disaster. Rotted rockers, who know what kind of shape the floors are in, and the uni-body is rotting. Knew all this going in. That was over 2 years ago. Mechanically the thing runs like a champ and is still on the road. I have put about another $800 into her. Came across the '00 for $1500 with 147K about 6 months ago. Needed work. Put about $600 into her to get her on the road. Body and uni-body are near perfect except for surface rust on the paint. Thing runs great. Needs some things to be perfect that I will address in the spring. Should probably stay away from some of the later '99's to '01's though. Bad heads. Poor casting causes them to crack. Google it too see what I am talking about. I chanced it and think I might have lucked out. So the best thing to do would be look for a '97 or '98. Things to look for. Jeeps are prone to needing new radiators. We sell a fair amount of them in the auto parts store I work in. You will want to go over the uni-body and find one with good rockers. You will want that has not been lifted and hopefully does not even have a trailer hitch. Make sure the 4 wheel drive works. Just cause the light goes on when you move the lever does not mean it is working. You will want to see the tire spin. Get a simpler Sport. One without Cruise, ABS, even power windows and locks if you can. Electrical can be a pain to diagnose if something goes wrong. While I also like Grand Cherokees they have more options like that and can be a pain down the road if things go wrong. I have seen more Grand Cherokees on Craigslist needing a tranny then Sports. If you get lucky you might find a Sport that has the Selec-Trac transfer case which means it has a full time 4 wheel drive selection as opposed to the Command-Trac that is just part time 4 wheel drive that most Sports have. It is always a crap-shoot buying a used car but if you take the time to look you should be able to find a suitable vehicle. I would not pay more then $3000 for one in really good shape. Which will probably still need a couple small things to be near perfect.

Actually both are great vehicles, although you'll likely get much better milage with the Forester. I'm the owner of a '99 Cherokee, currently with 210,000 miles and it has been the most reliable vehicle I've ever owned. I'm diligent about the maintenance and over the 15 years of ownership. Outside of normal wear items (spark plugs, ignition wires and rotor, brakes, some suspension components, etc), I've only had replace the starter at 208,000 mi and an idle control valve around 150,000 mi. While my case is purely anecdotal, the 4.0L six is well known for its longevity.

The automatic transmission used is an Aisin Warner (Toyota) AW4, which is generally considered quite reliable. The design is quite similar to that used in the mid-90s Toyota 4Runner and 4WD pickups.

There are two common issues with the Cherokee, which are not very expensive or difficult to repair. 1.) The crankshaft position sensor tend to fail at some point. 2.) The wiring for the speakers in the front door has a tendency to fail. Replacing the speaker wiring isn't very difficult.

Of course, if the vehicles you're considering weren't taken care you may have a much different experience than me.

Hands down, the Subaru. Jeeps have made some improvements but they are extremely UNreliable. Hope this helps

I have a 2001 Cherokee XJ with a list of issues yet it starts up and goes everytime. Unless a sensor dies, but very easy to replace and only a handful of sensors really fail.

The Subaru will probably be much more reliable. However, since these are used, it depends on how they were driven and maintained by the previous owners.