Since my last reply 8yrs ago i have been towing caravans and boats a lot. And used 4 other Subarus, 3 Outbacks and one Forester. Still have my -06 Outback as on my profile
And a 2017 Outback diesel which is a dream.
Worst towing was with a 2012 manual diesel Outback over the alps in Germany, Austria, Slovakia and back through Croatia, Italy. Had my big caravan with a lot of wind and 1800kg. On the highest peaks it felt like i lost half of the engine power due to thin air i guess...
But all was well anyway