Helpful advice: I would go for the 99... the mileage isn't as big of a 4.0 killer as the 0331 heads.. but the bottom line is it's your decision and you need to go with the one that seems better maintained.

more helpful advice: Don't tell us to check OUR pride at the doors, you're on CHEROKEEFORUM.COM where people who are very enthusiastic about CHEROKEES and the associated activities are. You're the one that's "At the door." We're already making it with a nice-smelling stranger in the guest bedroom upstairs.

 

What he said and make sure the body looks relatively rust free. According to where you are located this could be a problem with salt on the roads and what not. But give a good inspection and it seems like in your description you like the 2000 a lot better. But of it were me i'd buy the 99.