I have a '98 Jeep Grand Cherokee. It's new enough to have well-sorted fuel injection, good AC and heat, old enough to have zero tattletales, nags, and subscriptions. It has the best sightlines, is comfy and roomy on the inside, and frankly relatively compact compared to many of the behemoths on the road today. If it ever dies I'm really going to miss it!
2001 Jeep Grand Cherokee here. It gets driven hard so it has some problems, and everyone around me keeps pressuring me to get a new car. I've looked, and I've driven a pile of rentals, and everything is just so awful. I think 2010 is about the latest model year I'd ever go.
So instead I'm getting a really sweet new motor built for mine. Still the same 4.0, but with updated components and a focus on improved efficiency. My target is 25mpg highway. ...and a little bit of hooning around the desert racing circuit maybe. :-)
Even with a fancy motor (and transmission), it'll still be less money than a new replacement vehicle, and most importantly, it won't piss me off all the time. With already-upgraded suspension, steering, and some electronics, it's kinda fun and quite capable.
The only thing I'm really missing is safety. Jeeps are pretty terrible at the moose test to begin with, and 2001 was too early for side curtain airbags. I think I can retrofit 2004 side curtain bags into mine, and I'm redistributing weight in the vehicle that, along with some of the newer electronic suspensions, should improve its highway handling.
