Pro Pride 1400 hitch - need help

The stinger won't insert easily unless the hitch head angle is level with the stinger. You should be able to adjust the head angle by adjusting the straps just like you would with the jacks. In the picture above it looks like the straps need to be loosened to drop the bars and allow the head to pitch upwards. The weight of the bars should allow for this once the straps are loosened.

As for the bolts contacting the head, should they not be installed the other way so that the threads are down below the head? The head of the bolt won't sit as high and should clear under.