A front hitch with a wireless camera on the back of the trailer make this type of thing child's play.
My problem with backing either the 19' Toy Hauler or the 30' motorcycle trailer is I can't see the sides of the trailer, no matter how far out my mirrors extend.
I've thought about adding two more cameras to the sides of the trailer. Many times I need to back the trailer between two other trailers with about 12" on each side and no time to unhook and turn the truck around. Without someone guiding me, which usually there isn't, it is tough "stuffing" it in such a narrow slot.