I traded in an Outback for a 2008 w/ 14,500 miles. Though exterior styling is bland (this doesn't have too be a bad thing) everything else about this car is great. It handles well with good power. The interior is very sharp and the third row seating is actually usable and accessible. I consider AWD a must for Wisconsin winters and the seats fold easily for tins of space. there is even enough room for a decent amount of stuff with the seats up.
AWD, six disc CD, aux port, leather, traction control and third row of seats. For the base SEL, this thing is loaded.
Very little. The exterior styling is plain, but that doesn't have to be a bad thing. I am getting some wind noice from the back right, but I've only had it a few weeks and it is still under warranty, so hopefully that can be corrected.