I think you are on the right track regarding your options. Remember that VW also offers the standard Golf Sportwagen in AWD for 2017 and it should get slightly better mileage than the Alltrack version. New Sportwagen is a pretty large car. Outback/Forester are both solid options. The Outback is pretty huge these days, so it may be too much if you want a small car. The Forester is a bit smaller in length, but more upright. Both of these options will sacrifice some mileage to the VW options and they have CVT transmissions, which aren't as engaging as VW's to drive. They do have a superior full time AWD system that Honda/VW do not offer. The Honda CR-V and similar mid sized SUV's are all good options as well.
I always tell people who are considering VW and Honda/Toyota that you have to think about priorities. With VW you get an extremely high quality interior and more engaging driving experience, along with classic styling, but the engaging driving experience comes with more "engaging" maintenance, so you have to pay to play. You might also consider the Mazda CX-5, which has some of the driving dynamics of the Germans, along with a high quality interior.
Whichever option you get, I recommend setting aside $1000 and getting a good set of snow tires given your job. Even with AWD, they make a big difference. FYI, I am selling back my 2013 TDI Sportwagen - which I love and have replaced it with a 2015 GTI. I am able to use the snow tires from the Sportwagen which makes it handle great in snow, and with a Yakima Skybox I can add cargo when needed.