I recently finished a dissertation on piracy in this period, and if you could get hold of a copy, Colin Woodard, 'The Republic of Pirates' is a pretty accessible account that focuses on Nassau in particular as opposed to the wider geography of piracy. Pretty sure google books gives a fair amount as a free preview. 'Captain Charles Johnson' (sometimes credited to Daniel Defoe) wrote a contemporary biography of many pirates 'General History of the Pirates', which includes a few illustrations you might find useful for the fashions (though in comparison to Black Sails or Pirates of the Caribbean you might be a little underwhelmed).

Off the top of my head it might be useful to think about the mixed character of the residents, some were former privateers, a lot became pirates after looting the wrecks of the spanish plate fleet in 1715. There were also those who just profited second-hand from the pirates: merchants who were essentially laundering stolen goods, bars, brothels etc.

As in assassin's creed, there were factions regarding the royal pardon. Hornigold didn't really view himself as a pirate-and persistently refused to attack British shipping, so willingly turned pirate-hunter; whereas Charles Vane is a better fit for the anarchic, lawless image of the pirate. One thing that fictionalised depictions rarely cover is the fact that many pirates at the time had Jacobite sympathies, and justified their rejection of Royal authority in these terms. Blackbeard's ship 'Queen Anne's Revenge' could be seen as this, there was even a governor of Jamaica (I believe he was called Hamilton) who at one point considered building the privateers/pirates into a Jacobite navy.

Hope this is of some use, enjoy your game, sounds fun

What was life like for the pirates there? How often did they go out and raid ships? When they were away, how long did it take? What problems did they face?...How superstitious were pirates, and just what kind of natives would they be likely to run into? How common were things like the voodoo that you see in Pirates of the Caribbean? What were the major ports in the Caribbean and West Indies?

That's a lot of stuff you're asking for there. To help, first take a look at r/AskHistorians FAQ that has a section for pirate history. Click Here. Also, the search box can help as well. Between what is actually listed in the FAQ and the search box, most of what you asked about has been addressed somehow.

...anything that might show off the actual fashions and attire that pirates and sailors would wear.

There is no good documentary or published book that does this well for the GAOP of the 1690s-1720s (that is accurate anyway). It's a subject that hasn't been studied well enough by any means. You can find people who have picked at it here and there online, but nothing large or solid. It wasn't until the 21st century that academics started to do more serious study of any maritime clothing in the Age of Sail at all. The best you'll probably get online for sources on clothing is this facebook group called "Authentic Pirate Living History", particularly check their files tab.

This is a little different but a good resource might be Peter Leeson's paper on the economics behind pirate practices. I believe it's called "Pirational Choice: The Economics of Infamous Pirate Practices." It rationalizes and explains why the Pirates did what they did essentially and it's a relatively easy read. It also references a lot of old news articles regarding pirates and such.