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I'd like to see some SERIOUS ENGINEERING ANALYSIS on the TORQUE MOMENT and DOWNWARD FORCES on the latch mechanism that engages your King Pin with this design concept.
Essentially, I see a FULCRUM effect with the pivot point being the leading edge of the trailer's Plate and Chassis. The Pintle...
Another thought would be to simply buy/borrow/use a DOLLY. Hitch the dolly to the Pintle Hook, back the Dolly's Fifth-Wheel under your "new" trailer, connect air and power, and pull away. No fuss. No muss.