I own a 2015 Outback, and often drive a Forester when I get a loaner car when mine is in for routine maintenance. (I stress routine, because I have never had a problem with it).
My impressions are that the Outback is heavier and has a more solid feel to it...I prefer the way it handles to the Forester.
The Forester has a great FOV and a more spacious feel inside. The XT version is really fun to drive, (but comes at the cost of lower MPG) but the regular version is just meh, IMO. If you prefer a higher seating position and tons of headroom, the Forester might be for you.
For winter conditions, I’d prefer the Outback. Even though I “only” live in PA, I live in a rural area with rarely plowed roads and lots of drifting when it snows, and I make twice-weekly drives to the Pocono Plateau, where weather conditions can be very changeable (whiteout snow squalls).
I run Blizzaks mounted on steel rims.
I also prefer the lower roof height as I regularly load one or two paddle boards on the roof in the summer. Do you want to ever load anything onto the roof of your car?
BTW, the new Forester (2019) is better....a little more solid feel, better handling. But a little to “techy” for me.....I am all for safety features, but the displays were too distracting. But if you’re looking at used, that isn’t as much of a concern.
Make sure your used vehicle has only been used out West....here in the East, the prolific use of salt (mostly very corrosive calcium chloride) on our roads has a very visible rusting effect...I was dismayed recently when I saw the underside of my vehicle.