What year is your hull again? It would never be wrong to go into your anchor locker, remove the bow eye, clean up that area. Then reseat w/ 4200 fast cure. But, with the gelcoat crack there, I would not want water to sneak in and intrude that lamination.
There are numerous ways to load a boat on a trailer: Wart suggested one technique. Like him, I would not use that bow eye to pull the entire weight of the rig onto the trailer/ bow stop.
Personally, I hand load all my boats: W/ my bigger boats, I need someone in the truck to back down while I hand crank. Like wart, I dunk the trailer so all 4 bunks are wet, then pull forward so the last 1/2 of my heavy load bearing bunks are submerged. I get the hull lined up perfectly, sneak off the bow, hook the bow strap to the bow eye. I crank. I motion w/ my hand for the driver to back down... I will have him back down twice maybe three times to securely load the boat on the trailer.