The main elements would have to include:
= Ships to capture and plunder. Will they fight to the death or surrender? Are they carrying silver bars (great), bolts of cloth (okay), or iron ore (useless)? Is anyone on board worth holding for ransom? Will you sink the captured ship, keep it and sink your old one, or split your crew, keep both, and start your own navy?
= If you have a decent-sized pirate fleet, maybe you'll try to attack a rich, well-guarded convoy (like the Spanish gold fleet), and make enough money to retire and let someone else become the Dread Pirate Roberts.
= The risk of encountering a navy ship, with the resulting choice to flee or fight.
= Coastal towns to pillage. Possible hostages to ransom.
= A pirate haven. This would include merchants to buy your stolen goods, taverns full of rum and rumors, retired pirates selling treasure maps, shipwrights to repair battle damage, and wenches. Everything has an exorbitant price tag, and every piece of information is probably untrue.
= Reputable ports that are probably too strong to attack, but where you might sell some goods and get supplies at a fair price, as long as they don't know who you are.
= Semi-reputable ports where the governor can be bribed or given a share of your goodies, after which that port is just like a pirate haven for you, only less expensive and a lot safer.
= Islands with tribal people on them. These people may worship you and give you gifts, trade their food and shiny gold jewelry for your fabric and trinkets, eat you for supper and shrink your head, or put a curse on you, courtesy of your friendly neighborhood witch doctor.
= Uninhabited islands where you can get fresh water and some provisions for free, capture some parrots and monkeys to sell, and possibly hunt for other pirates' buried hoards.
= Ambitious NPC crew who challenge you to a duel for the right to be captain.
= Other pirates. Can you trust them to work with you, or are they setting you up to be their next victim?
= Morale factors. The longer you go without a victory, the more likely your crew will mutiny. Multiple successes may persuade NPC pirates to join you and add their ships to your fleet.
= The option to start as a privateer with a letter of marque, and let many fat victims go because they fly the same flag you do. In exchange, the navy is not your enemy, and you can dock and provision at reputable ports that fly your flag.
= The local governor may offer you a fat commission to hunt down an even more wicked pirate than yourself. Or he may put the price on your head instead, and every other pirate becomes a potential enemy.
= The occasional eccentricity to keep things interesting. Real-life examples: Bartholomew Roberts capturing a ship just because he wanted the crew's hats; Edward Teach blockading a town to get a box of medicine; and Stede Bonnet becoming an inept pirate just to get away from his nagging wife.
