I’d be happy to help too. May I suggest looking to the TV show Black Sails for more Assassins Creed Black Flag style inspiration. The design of Nassau in the show and the way the pirates are portrayed is what drew me to the server in the first place.

^^^Fort Nassau –  The Old Fort of Nassau was a fort in Nassau, Bahamas, first built in 1697 and lasted for nearly two hundred years with a rich legacy of history until it was finally demolished in 1897 …. It was at the ruins of this fort on its western wing that the British Colonial Hilton Hotel was decided to be built.

https://en.wikipedia.org/wiki/Old_Fort_of_Nassau)