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There is a post on card cheating already, but basically use the best odds in your favor. That would mean cheat when you can see the most possible cards in your favor and you have less chance a pulling a card on the table, or blackjack.
Best rep is shooing sails and then using broadsides. Beware though shooting ships at a distance with lightning, wait until it reaches your radar before the final shot. Else you will likely get nothing for it out of range.
As for other skills alter them in the same way like the ship and cannon, you get more rep and work several at once. Use less damaging attacks and more of them.
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