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As I think I've proved before but...
How high with the riser blocks be? Will the cleat be higher than the winch or about level with the midline? Is it a self tailing winch? I think you'd want the sheet lead to be as straight off the winch as possible. Certainly you don't want the lead to be down toward the cleat or the sheet likely won't stay put.
Can't answer question number two with even a wild hair guess.
If I was doing it, I owuld be inclined to drill slightly larger holes, file them with thickened epoxy and redrill for the riser blocks/cleats. By all means put backing plates under them to spread the load and bed the riser blocks to keep water from seeping under.
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