1. Pirates don't wear armour. None. If you fall overboard wearing even leather armour you can be counted off as [censored].
2. Pirates use sloops. The sloop is the only ship small, fast, and maneuverable enough to suit the needs of the pirate. Anything larger is too slow and/or ponderous.
3. Pirate weapons will probably be pretty good. They spend their entire existances in the pursuit of wealth, and they use that wealth to upgrade the things they use the most: weapons.
4. Unless you are an admiral in somebody's navy, you do not command 8 ships. Pirates do not have the necessary administrative skill to manage 8 ships. Even if they did, i can guarantee that some ambitious young pirate on one of the ships, or one of the captains will get sick of you hogging all the glory and sail off into the sunset in search of his own swag to steal. I suggest you limit yourself to less than 5 ships. Preferably 1 to 3.