I'll just say I would avoid the VW, they have have a pretty bad reliability record. That's from hearing from other people complain about them online, and also from knowing a few people that own them. Not as bad as a Range Rover, but not much better either. A lot of minor issues (especially electrical) that add up to quite a bit of money and frustration.

Between the Ford and Subaru, I'd lean torward a Subaru, but then I'm biased because I own one. They are popular for a good reason, and it definitely isn't their looks. But they have earned the reputation as being a very reliable, no frills type of car. The Ford is newer, but a difference of 25K miles on a used car really doesn't mean a whole lot. How the car was maintained and how it was driven and cared for are a lot more important than the number of miles. The Ford escapes did have a lot of problems when it was first introduced, but most cars do on their first model year.

Really depends on what you prefer, the Escape is more SUV-like while the Outback is more of a station wagon. For traveling off-road, I'd probably give the edge to the Ford because I know the Outback has some huge overhangs, but the differences are minor and neither of them are going to be great off road. Both of them are essentially lifted sedans. On road I think the Outback will be better in terms of fuel efficiency, handling, and just general road manners because of the lower center of gravity.