Can i tow an enclosed two place snowmobile trailer with a 1997 outback?

Hello, considering buying a 1997 Outback. Would like to know if I would be able to pull a loaded two place enclosed aluminum snowmobile trailer without wrecking the tranny.

There are things to consider... automatic or manual transmission, tongue weight, wind resistance (being its covered), and the two big ones are; weight of fully loaded trailer, AND how wide is it, you need to see past it in your side view mirrors.

I would be able to see past it with extensions. Automatic trans. Looking at a total of 2000 lbs. There is some wind resistance, not alot. I just don't want to wreck a tranny.