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Why not be able to hire cannoneers as well? They could have different types of cannoneers (different ammos), all with different rank (1-5 or 1-3 or whatever), with the appropriate cost. You could hire a ship hunter maybe, who'd know how to find a ship you're looking for.
I like the idea, and am thinking they could make you have to pay to hire a broadside man, with the upside of increasing the pay off of each run. Iunno though.
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