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Hello,
I understand your reluctance to carve away more wood. Is this a 1-part halyard? Is the problem that it's too hard to hoist? If so, consider deadending the line aloft, then go down to a small block or lizard on the sail, then back up to the dumbsheave. You'll double the purchase, overcoming much of the friction.
Mounting a cheek block would probably not make for too much side moment, but it would be foul on one tack, yes?
Fair leads,
Brion Toss
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