Dont think its intentional. That truck would be pointless without proper handling of simple semitrailers. You cannot even connect the large fuel semitrailer because its colliding with the "winch package".
I'd move the 5th wheel a bit back, or make the winch package a bit smaller - its not much needed. And give it stock either a monster winch or remove the rank 17 "lock" way down.
By the way, explains strange steering yesterday as I had the flat semi and tried to make a sharp turn. Works on a flat surface "just", but not really if the tail is on higher ground as the truck. It can "hook up" as you have shown.
Edit: by the way, I do like this truck. It has some character. It has even spotlights when reversing, so you can see where you do in the dark. And it would be even "better" if one would allow it "standard fog/rooflights" without the silly beacons.