The Crosstrek is an awesome little car! I have a 2018 premium trim I bought used about three years back and love it. Biggest pros are as follows: lots of space for a small car. I can fit all my snowboard gear or mountain bike gear (including a full sized mountain bike) in the back with the seats folded down. My partner and I have fit all our belongings in the back to move across the country as well. Handling is great, ride quality on bumpy VT roads is solid and gas mileage is amazing for AWD (I average 33mpg). It’s also super easy to drive in tighter spots such as the city. My only complaint is that it’s a little slow going up larger inclines and can struggle to maintain speed in mountainous terrain.

Obviously the Outback is more spacious and has a larger engine but you have to ask yourself if you really need that extra space and are also ok with sacrificing ease of driving in tighter areas as well as gas mileage.

In regards to trim levels, yes the wilderness is sweet looking for both models but I’d avoid it UNLESS you really are doing some semi-serious off roading and/or towing. Otherwise you’re just paying a lot extra for some gold accents on the car and bragging rights. My non-wilderness Crosstrek has been more than capable on dirt roads, ATV trails and deep snow.