It sounds like your limit switch is set a tiny bit too high.
When adjusted properly, the jack screw should stop lifting a few millimeters BEFORE the pin can be insterted. You squeeze the wires together by hand to lift the motor the last little bit against the gasket and then insert the pin. The motor's weight should sit on the pin, not hang from the cables. When the pin is in place there should be just a tiny bit of slack in the cables.
That's the way I was taught to adjust it, and it works.
Underway, off of Long Island,
Headed to Boston