Depends on a whole bunch of things. How big is the 5ver going to be? is the front of the fiver going to be on the up hill side or down hill side? It is my opinion that if the head of the fiver is going to be on the down hill side then it might be less stable. Once those landing gear are raised more than normal things start to get pretty shaky On a big rig even shakier. As far as hitching up it would be easier to hitch a 5th wheel than a trailer on any type of terrain I would think. I have had both. Never had a situation that was hard to hitch the fiver up to.
