Re: Guns...Will they kill it?
Yeah, I like the idea of having your own ship. It'd also be kinda cool if they based 2 in a more islandic situation... which makes no sense. But I mean that it should be based partially in the Caribbean, Meditterranean, Pacific, Indian (their analogs, at least), and allow you to go to Iceland and Greenland (which I think might already have their analogs in Hook Coast and the Northern Wastes) as well, and other islands in the North Atlantic.
Then you can sail around all piratically, attack pirates, attack other ships as a pirate, defend against attacks from pirates, defend against attacks from Revenue Cutters and naval forces, and fun things like that. Then you can also have fun with cannon and boarding.
And on dual wielding-- I think it might, real-world-wise, be possible. All I have to base this on is fictional historical and time travel books, but I have read of wheelock pistols fired dual-wielded by cavalrymen, and wheelocks are about as old of pistols as you can get... so I think it might be possible. I have also read of them being fired one-handed, by one-armed characters. On the other hand, I AM TALKING ABOUT FICTION, so it is, of course, of dubious legitimacy.