Subarus are good cars, but a bit flawed. We had a 2000 5mt Forester and a 2014 cvt Outback. The Forester was my favorite by far, but did require head gaskets, clutch, etc. I sold it to my neighbor and she is still driving it at 240k. It's a lot of fun with the EJ25 and manual and refuses to die.
Build quality and reliability are not Toyota good but better than a domestic car. They are also stuipid-easy to work on. Struts, oil changes, etc are very easy. Our 2014 OB had some annoying problems like needed rear shocks every 40k, new caliper brackets in the front, and new head and fog lights yearly. But zero big issues.
IMO if you want a reliable, economical, and versatile vehicle, get a NA 2.5 Outback. It's a very sorted platform, capable enough for soft roading, drives great on the highway, and gets good fuel economy. The Wilderness will be less reliable with the FA24 turbo and have a sizeable MPG and reliability penalty. CVT reliability with the turbo has also been mixed. The unibody platform flexes poorly and will always be handicapped offroad regardless of the lift. I would personally get a 5th gen T4R over a Wilderness.