My dad has a 2011 Outback and my brother has a 1995. They are both very good cars -- reliable, good in the snow, solid handling. At $25k you'd probably be looking at a 2010+ 2.5 or a pre-2009. I haven't driven the 2010 2.5, but I have to imagine it's dog-slow. The same engine as in my '08 Impreza, but with a lot more weight to haul around. It does get 24mpg combined per the EPA, which is pretty good for a an AWD car of its size. I actually like the look of the 2009 and earliers better, and you can get the sweet 2.5XT model. But obviously an older platform and IMO they don't ride as nice, and are a little smaller which can be good or bad depending on if you like the smaller footprint or want more space.

If you could find a 2010+ with the 3.6 they have really good pickup, though MPG drops to 20. Hopefully the new DIT motor will make it's way over here, that thing is sweet.