Holy cow, you're not even 25 yet? I never would have guessed. Good god I feel old... [&:]

Anyway... if AWD is a must, have you considered perhaps a slightly used AWD Charger or Magnum? I realize they might be a bit pricey still, but a V6 model shouldn't cost much more than an AWD Fusion, even with your family's discount.

If I had to choose one of your choices, I'd probably be inclined to go with the Grand Cherokee, even though they are a hit-and-miss when it comes to reliability - I've known some that absolutely love them, I also know some that swear they're the biggest POS ever made... so if you go the GC route, select very carefully. As far as a Liberty, I guess there's nothing really wrong with them, just never been a fan.

BTW... when did they ever make an AWD Intrepid? My parents bought an Intrepid new in 2000 (still have it), I thought I knew those cars pretty well... I've never heard of an AWD option for those.