This is where a roller-floor could come into its own. Set the skids where you like, secure them with E-straps and load bars as needed, then when you get to the receiver just roll those puppies to the tailgate. What could be easier? But, securing the freight IS a problem with a roller floor, so I reckon we do the best we can.
I agree that Ford messed up a long time ago with the overhang issue. The Chevies have the rear axle set back, and it DOES make a difference. The overhang in an extended Ford E-Series could be enough to make for handling issues as the front end gets too light. I don't know-- because I haven't looked that close--- at the new Transits, but if Ford is still doing the same thing-- setting a longer body on the same wheelbase as the standard body-- there will be handling issues with the extended Transit. Maybe worse since the taller body might encourage more weight to be placed there.