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).

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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.

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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.