Steer clear of the '99-'04, 2.5 liter engines - those are guaranteed head gasket issues.
My brother just traded his '15 Outback for a '16 Ram. After a recent trip in it with his new bride out to western PA, the decision was made for him. The thing was a gutless slug (4-cylinder) - could feel the lack of HP on every hill. Only put about 6k miles on it. Also hated the CV transmission. Was a strange, quirky thing. Mileage wasn't all that great for a 4-banger either.
Definitely overpriced! Everything is today. Trucks are selling for $65k and up! Ridiculous.