Hitching and unhitching a 5th wheel

Assuming the pinbox and hitch are capable (most are) of hitching at the angle you want, the only concern is the landing gear being bent from side to side - line the pin up VERY well, have the pinbox height within ~1/4 inch of the hitch, and don't hit it to hard. I would have the pinbox a little high, until the hitch is under it, then raise the landing gear until it makes contact - at an angle tire chocks don't hold the trailer as well when hitching. As far as the frame/springs/rims/tires you will have more stress in a single u-turn then 20 sideways hookups.