I could see doing that with my deuce. You just have to be comitted to the job and have confidence in yourself and your equiptment. Skidder guys do that everyday in some areas.
Done that with the deutz and tote box when I have a big load. Left and right brakes are sure handy..but since doing that a couple times I just back up hills.
Long time ago, my paw in law had 427 Chevy trucks with the twin transmissions, in a hard pull they would clear the front axles easy, steep hills called for the skidder just to keep them in the road. even if it were dry.