FYI most front receivers are rated at 500 lbs carrying, remember that whatever tongue weight you have is on the front suspension...but your TT is relatively light and with your rig it should be OK. "Straight line pull" refers to winching, where there is no tongue weight being applied at all.
I would say your idea could be do-able if you can solve the visibility issue. A camera on the TT would work great, but then again, if you add the camera you can just back down the hill and not need the hitch and wiring on the front.
