You may want to give the Outback's CVT a couple years of field testing before towing much with it. It is a new transmission, and is a belt-style CVT unlike Nissan's Torroidal CVT. The belt-style CVT have the potential to generate lots of heat. I haven't heard of Subaru having problems with it yet, but it's pretty new and I think its rare for Subaru owners to actually tow.
FWIW - the Tribecca has a traditional automatic still, and also has more carrying capacity than the Outback but the overall footprint is pretty close.
