I was thinking much the same thing as I thought more about it today. The cradle is pretty flat, so unless the Outback has the rings pretty much all the way down all weight of the TI would be transferred to just the rings, the cradle will be lifted off the crossbar. Which may be fine, will have to see when it arrives.
Can't be bothered to fit it to the Outback yet - there's a cold rain outside and I'm not too eager to roll the trailer out of the garage to unload...
I've been using a standard kayak cart up 'til now with the Outback - a bit clumsy but it worked. I will try this one Tuesday - full moon night, and the weather's supposed to be relatively warm (58F for a high) so a few of us are headed to the lake for an evening paddle. Sure wish I had my TI already, would love to stretch out on a tramp watching the moonrise...