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It might work but how are you dealing with ship motion (yours and enemy) since all that changing at the helm is going to basically bring your ship to a halt (or at the least drastically reduce your speed)?
Don't the sails go up/down (not sure of direction, but NOT work) each time the helmsman leaves the wheel?
And not for nothing, but there's an awful lot of "I need" in that guild description. It looks like you want a permanent crew instead of a guild. Some might like it but I will respectfully decline.
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