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First you need the roller out of there so you can asses everything with a clear view.
When you have two nuts, the first nut removed will in most cases clean the threads so the second nut comes off easily. Especially with stainless, make sure you use a lube when removing, preferably oil or grease, not wd40 or similar, as stainless to stainless with a load on it will gall and eat threads or jamb them tight enough to feel like they're welded.
Two jamb nuts at the end of the screw will allow you to hold the screw while you loosen the originals.

After that you'll have to inspect everything to determine the best approach.

Just from the pics, I'd think about grinding the breaks back to solid glass to get rid of any splinters, delamination, or fuzz, grind a bevel, apply the fiberglass, then cut a plywood or aluminum triangle to spread the load as much as possible to the unbroken areas around it. Possibly some gussets tabbed in to transfer part of the load to the hull.
(plate on underside of roller mount dip, with bedded spacers beside to transfer the load to the deck)

Ken.
 
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