caulking

when I cleaned out the caulk from the shroud deck straps there’s a fair amount of play in the deck penetration and the cover plate holes are blown out. If I block the strap to center the hole and caulk I’m not sure it wouldn’t move. Any suggestions appreciated. Thanks Jeff.

After searching the forum for "Do's and Don't" I found a lot of variation on caulking but was mainly on installation. Rub rail design is as varied as boat construction and size. I am not even sure of how my boat deck hull is fastened and water proofed to the main hull. You can see where...