The ZJ Grand Cherokees (1993-1998) are not bad at all. There are many of them still on the road today with 250-300k miles, so they can't be that terrible.
They do require maintenance such as transmission fluid changes every 30k miles, coolant changes, transfer case fluid changes, etc. If those aren't done then you can expect to replace the transmission. A secretary at one of the school districts I work at has a '98 Laredo 4.0L with almost 300k on it, and it is all original drive train. She bought it new and has serviced it every 30,000 miles at the dealership.
The electrical stuff can be hit or miss. Make sure the connections are clean. Bad grounds and dirty connectors will make for a bad time on these things, and also make sure the battery is in good shape. As previously mentioned, check wires in the door jams because from repeated use they can wear on the doors and ground out, causing the power stuff not to work.
The A/C not working is common once these get to be 20 years old or so. You can find a compressor for under $100 online.