I wonder if canvas guy has tried reverse loading the Outback yet?
The original issue was the kayak kept sliding off the c-tug cart.
I know my suggested solution will work as I have encountered the same issue on a steep incline with my Outback......and looping the straps under the carrying handles prevents any additional movement on the cart.
Regarding the c-tug video on proper threading the strap through the cam closure....I have followed the instructions to a "t" and it does not work unless the cam closure is located on the side of the hull for support.....this is why I changed the strap over to the NRS cargo strap......it is not dependent on the hull, placing pressure on the tail end of the strap, to prevent the strap from slipping in the cam closure....try a wet nylon strap in the cam closure to see how slippery it is.
Tom has a point and I am sure he is happy with his solution.....I prefer my solution as the c-tug is better suited for a strap secured around the base/support vs a bungee hook and the ease of tension adjustment on the strap.