Bolts
Hi again,
The primary load on those bolts will be in shear. Even if the deck plate doubles to support halyard turning blocks, it is most unlikely that any halyard would provide even a 1,500lb vertical pull; tensile strength of a 5/16" bolt is about 8,000lbs.
1/4" wall bushings would be fine, and on all the fasteners. Thicker is better.
Fair leads,
Brion Toss
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