I'd say that what lck?????? did on his boat looks near perfect.
Looks like he used a short 4x4 cut to fit the opening (where your rubber stopper fits now). However, his short 4 x 4 might be need to be made longer for you... by a few inches. Or, perhaps, you might use a 4 x 6.
That way, the long, carpeted, cross piece would wind up a couple of inches further back. That would give you more clearance to crank the handle.
However, if you do push the boat backwards with whatever "fix" you do here...better check to be sure the stern is still fully supported by your trailer. A fully supported transom is the right way to do it.
So...if your "fix" in the front causes issues in the stern, then you may have to extend or move your hull supports towards the rear.
Rich
p.s. Your grabber handles might get in the way. Your cross piece might have to be shorter, due to the position of the grabber handles. R