Hey, Scotty! I want to know your opinion on the old Jeep Cherokees with the 4.0L six-cylinder engines. I've heard great things about them, and they seem to hold their value, but being a Chrysler product, I imagine that the transmissions probably aren't great. I think they're really cool, but I don't think I could bring myself to buy a vehicle made by Chrysler.
Ok, you are right about the transmissions. They are noticably weak. If you are willing to replace the transmission, as long as you get a great deal on it, it is a fun toy to have.
Old Cherokees (XJ's) built prior to 2002 back to the late 80s used automatic transmissions designed by Aisin and Borg-Warner and are very reliable and robust. Aisin makes most of the transmissions for Toyota. Prior to that I think the autos were manufactured by Chrysler although I'm not sure since at that time Jeep was still owned by AMC. XJs are wonderful vehicles and good, rust-free ones are becoming more scarce and increasing in values.
The XJ Cherokee was sold in the U.S. from 1983 though 2001. Most of the later models have the 4.0 and Aisin-Warner 4-speed automatic combination (though manual trans was also available, as was a 4-cylinder engine paired with a Chrysler 3-speed automatic).
The 4.0 six is the ultimate evolution of the Rambler 232 cid six introduced in 1964 and is a robust engine that can go hundreds of thousands of miles with a little care. As roscoe mentioned, the Aisin-Warner transmission is also very reliable, pretty much bulletproof. (Squigward may have been thinking of the Grand Cherokee upmarket model, most of which used weak 4-speed Chrysler transmissions.)
Early models (1984-1986) were equipped with a 4-cylinder 2.5L AMC engine or a 2.8L Chevy V6, paired either with manual trans or Chrysler 3-speed automatic. (The Chevy engine, to be charitable, is not well regarded.) The 4.0 with Aisin-Warner 4-speed automatic was introduced in 1987.
The 2000 and 2001 Cherokees have a known weakness in the cylinder head which tends to crack, permitting coolant to get into the oil and causing serious engine damage. The 2000-2001 models also have individual coil pack ignition instead of a distributor, and 3 catalytic converters (some 2000s and all 2001s), two in the exhaust manifold plus the one underneath the vehicle. Both part-time and full-time transfer cases were offered.
You need to take into consideration that although these are reliable vehicles especially with the 4.0/Aisin-Warner drivetrain, the newest XJ is 20 years old so there will be a variety of old-car type issues to deal with, and you have to be careful about rust.
Here's a good resource for people who own or are interested in owning an old Cherokee:
https://www.cherokeeforum.com/