An excellent idea...I like bringing a character from next to nothing to absolute ownage!I've been looking at some charatcers, i have put Pitt with the Colonial Schooner as his starting ship. I want one of the character's to be a difficult start where you have a Gun Boat and next to no money. :will
I can confirm starting with Alexander who has the Gunboat and playing as the pirate nation on commadore is almost impossible. As any other nation you would find it easier since you have the option to trade but with the pirate nation its not so easy. Your best bet is finding and boarding a Bermuda Sloop, selling the Gunboat if you have a officer to sail it and sell all cargo from both ships along with the guns off the Gunboat. Hire as many crew as your ship can hold and search for a Lugger. Slowly working your way up. You'll need to have at least double the boarding crew of any ship you wish to board because one hit and you can be killed with the heavy attack, and the same with a shot from a pistal.
or you could just use cheatcodes...LMAO!!!