I had similar issues. I installed Armstrong compression deck plate. Had to cut bigger hole in bracket to fit deck plate. You only have one chance so go slow and measure twice. Been in the water for a month and it's doing great. I wanted easily remove able plate so I could remove water from inside bracket if it started to fill up again. I keep the boat in the water and I don't have easy access to my trailer.
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After I looked lore closely I realized my issue wasnt the plate but rather the bracket started gapping away from transom in spots. Might have been bad caulk job finally giving out or wet transom morphing. I know the transom is a little wet so that likely is root cause. I'm trying to get another summer season and replace transom this fall. So I put 5300 around outside of bracket. First time it didnt stick so next time I did a lot of prep to remove bottom paint and other grime. Now I don't know if it will ever come off.
I had similar issues. I installed Armstrong compression deck plate. Had to cut bigger hole in bracket to fit deck plate. You only have one chance so go slow and measure twice. Been in the water for a month and it's doing great. I wanted easily remove able plate so I could remove water from inside bracket if it started to fill up again. I keep the boat in the water and I don't have easy access to my trailer.
Save More on Your Armstrong Watertight Compression Deck Plates at Fisheries Supply. Excellent Customer Service, Ready to Ship. Marine Supplies Since 1928!