Just had to go through the car process recently, as well as two other family members. I was coming from a 2011 Legacy (outback is the same, just higher up) and I knew i loved the ride, just wanted something with clearance - so, not a VW, but I can share my thoughts, as I too had the "should I put money into a newer car with a CVT" My things to consider:
1) All car models/brands have problems (CVT or Not) - go on consumer reports and read about it. Everyone has recalls and reliability issues. Nothing is perfect - not toyota or honda. You can look at the overall satisfaction of each vehicle plus the reliability percentage. Any new car you buy will come with a warranty. If you buy certified pre-owned you will get a 7yr/100Kmiles warranty and you can extend the bumper to bumper to match that for additional cost. Cost of ownership will vary between brands in the long run, but if you've got a german car, you're probably used to that. My Legacy "Wear and Tear" repairs cost the same as a Toyota sedan. Not sure about parts these days but with a new car, you shouldnt worry about that.
2) Test drive everything you are interested in. Try Subaru, Toyota - whatever other cars you are curious about. Love the car you drive. I'm used to the CVT and actually prefer the smoothness of the ride for long distances. The only other transmission I prefer over it would be a 6 cyl!!! I find 4 cylinders to whine too much for me and lag behind on shifting. Subaru's other cars are nice too. OB and Legacy are made in USA (of course the parts are Japanese). Forester, CT, etc. made fully in Japan.
3) Subaru give you the best price for what you get. The touring models are really nice. Hands down, subaru's AWD system, plus Xmode in all the vehicles, is amazing. If you need something with better AWD, nothing beats subaru (esp. with mpg, my opinion). If you don't need it and drive around towns and paved roads, other awd might be sufficient. For you to decide. I commute A LOT and I prefer the AWD all the time. Wish I had leather seats of the touring! The safety features are nice. Price wise - you can look at other brands/models - but subaru will still be best bang for buck. - AWD, Gas Mileage, Safety, Driving Comfort, Cargo Space.
4) Resale value is high for Subaru, so if you ever decide you don't want it anymore - you will have no issue selling it.
So, if you plan to keep the car for 20 years, then consider overall. At the end of the day, it's your opinion and how you feel about it. If you plan to keep it for 5 years and switch, I wouldn't even hesitate and go test drive it!