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I take it that the PC versions has differences in how the special figureheads and guns work? In the SNES version all you had to do was get both the economy and the shipyard to 1000 each. It did help that the port was allied to whatever country you hailed from but luck really didn't play a part in it. I almost never donate funds and have gotten the figureheads and cannons from all over the world. But only once per port. The special ships could only be gotten from certain ports. Bristol and Bordeux ( something like that at least ) sell the Barges but they are way to slow and hard to handle in a fight.

I did find that the duels went better if you understand all the swords and what the special ablilites are since that way you are pretty sure what the other guy will use as an attack. The basic formula goes like this: You parry against a thrust, block against a lash, and dodge against a strike. The ones that inflict the most damage is: Dodge against lash, block against thrust, and parry against strike. So try to fake him into using a defence that will inflict the most damage to him.