First, read through
THIS THREAD. It's more or less the same question, and it might help you find what you're after... or just confuse you more.

If AWD is your most-desired feature, I would go with a Subaru Impreza and not look back. New or used, the AWD system is the same, the only difference is the bodywork. A used Legacy or Forester is a good option, too. All have the same AWD system, and as mentioned it's the best in the business.
I think a Ford Fusion can be had with AWD for under your price cap (don't quote me on that, though!), but of course it's not a wagon.
Matrix/Vibe is a good vehicle, although the AWD system is nowhere near as good as the Subaru one.
Honda Fit, while smaller and FWD, is surprisingly roomy. And it scores high in reliability and safety with six standard air bags. Good on gas, too. And since it's a Honda, good resale value is inherent in the name - I've seen used Fits on dealer's lots asking more than MSRP on a brand new one. Owners here report very good winter performance on proper winter tires.
But really, very little beats the reliability, safety, and winter prowess of the Subaru lineup. They tend to have quite good resale, too. I'd put a Subie at the top of your list, honestly.
