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If it were me, I'd leave the broken stud stump right where it is and stop messing with it. I'd drill a new adjacent hole, 5/16"+ in the side plate and with the side plate in place as a drill guide, a smaller hole into the block side of suitable size for a 5/16"-18 tap. Position the new hole just beyond the repair plate so you don't disturb it. That way the side plate will be nearly as secure as original.
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Neil
1977 Catalina 30
San Pedro, California
prior boats 1987 Westsail 32, 1970 Catalina 22
Had my hands in a few others
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