I am constantly scanning CL, autotrader, cars.com, etc. to get a read on prices. I got to be honest, if I saw a 2007 Outback 5 speed with 69k miles for $8500, I'd snap it up. The further south you get from 10k, the less the VALUE you get for the COST. The VALUE / COST equation is, to me, as important as the actual cost. If you were the active sort, keep your stuff in good shape, I'd just keep the car. It's probably going to cost you little in maintenance for a long time, and you aren't rolling the dice on something used and cheap. I haven't seen ANY Honda Fits / Toyota Yaris', etc. for under 7k, and the ones close to 7k were very high miles / base models (and the Yaris isn't particularly fun to drive). As far as MPG goes, yes, there are cars that get above 29 MPG but 29 MPG for a fairly heavy (respective to the cars you are looking at), awd vehicle is not bad. Unless you go to a very old Metro, Civic, etc., the highest mpg cars are still a few years off from being cheap.
Now if this is a case of wanderlust, then by all means sell the car (but I think you can get way more than 8500 for it). Then take the cash and start shopping.