If towing is really your thing, go the Forester.
I'm beginning to wonder if the Forester is the red-headed stepchild of Subaru's lineup. Per the 2015 manual, it's rated for a 1,500 lbs towing capacity, full-stop. The Outback, as you noted, goes much higher, assuming your trailer has brakes.
The problem is that the Outback as I would want it is a tad past what I would like to spend on a car, and the 2015 is the new generation with the better MPG.
Sorry, I heard recommendations were good, but obviously that's pitiful as well. I never looked at a Forester personally, I was really interested in an Outback until I saw what a trainwreck its capacities were. Can't really recommend any Subaru then.
Obligatory minivan bump. Best tool for the job.
“I think minivans are a ridiculous invention for carrying 60-pound kids, but great inventions for heavy construction work.” Here’s my van collecting 1200 pounds of logs for firewood.
At this stage with plenty in the bank, I have grown soft and have a bit more truck than I need. It’s a 1999 Honda van with 140,000 miles on it. I bought it for $4,800 four years ago, and current market value is maybe 3 grand. Less than what the juniors with no money spend on their wheels and tires alone.
And this thing can work. I have carried over 2,500 pounds comfortably, it can lock up a full selection of tools and keep them dry, and with the seats out you can close the rear door on 12-foot pieces of lumber or a stack of 20 full sheets of plywood. This is the truck I use now, but most of my carpentry career was done with something far less luxurious.
So you could get an AWD Sienna if you don't think FWD with snow tires will cut it.
With a medium sized pet carrier in the mix an Outback likely won't be big enough unless you strap the stroller to the roof.
Continuing on the minivan theme.... and I don't need to get new here at all, but I would like to think I would keep the car for 10 years after purchase... Odyssey or Sienna?
Well if you need AWD then there's only one choice. Otherwise I'd say a draw between the two.