I bought a '99 Grand Cherokee for my winter car last week. It was in decent shape for a '99 with 140k miles on it, and most importantly no rust that I could find. But there are little things here and there that need taking care of. Since it's a cheap winter car, I've been messing with fixing them myself. So far I have:
11/25/2013 - installed fresh wiper blades front & rear
11/25/2013 - put on a steering wheel cover over the ratty factory leather
11/27/2013 - fixed a stuck driver's seat height adjuster, using a hammer
11/29/2013 - installed tailgate lift struts
11/30/2013 - got tape deck aux adapter
12/1/2013 - installed hood lift struts
Stuff I still need to do:
Have replacement key fob I got for 15 bucks on Amazon programmed by the dealer (it only came with a regular key no fob).
Polish headlight & foglight lenses and put in nice bright bulbs (already have the supplies).
Re-attach door frame weather stripping with some adhesive (already have the supplies).
Fix a grinding noise under heavy braking caused by the transfer case shifter cable dangling too low after a clip that holds it to the body breaks and it rubs on the front driveshaft, by zip-tieing the shifter cable back in place.
Replace the climate control panel with one that has intact recirc button—mine the front of the recirc button has broken off which is pretty common. These go for like $60 on ebay.
Replace the tailgate glass lift struts—I did the main tailgate lift struts but didn't want to buy the ones for just the glass.
I love late 90s Chrysler build quality.