My turn. I'll reiterate my strong recommendation to read The Sea Rover's Practice: Pirate Tactics and Techniques, 1630-1730. My previous review is here (not that my reviews are masterpieces, and this was my first in a very, very long time).
Recently, I had the very fortunate opportunity to exchange email with the author, a former Navy SEAL. What I learned surprised me: I was one of the few scholars who found parallels between then and now in terms of privatization of force and insurgent warfare. (Maybe mom was right.)
If you're interested in historical examples of privatized force and insurgent warfare remarkably similar to today, pick up this book. If you're interested in a book that draws from period diaries of actual pirates (how cool), along with detailed discussion of their daily operations and tools, pick up this book. If you think 1648 was a magical milestone in the evolution of "state" ownership of warfare, don't both because this will burst your bubble.