Privateers

Stop calling them privateers, they're just pirates! Necks in need of a good noose!

— A one-eyed, one legged merchant captain

Privateers are the mercenaries of the sea, hired to disrupt shipping for their employer's enemies, be that a country, city-state or even a specific rival merchant company. Or so goes the theory. Most operate more as pirates, treating their employment more as protection money paid to grant safe passage to their employer's ships. They are both feared and scorned by merchant sailors in equal measure, often running their ships to the point of sinking before capturing a new merchant ship and scuttling their old one.

Skills

Successful privateers are principally skilled in the art of theatric violence. They are plenty vicious, of course; no person joins a privateer crew who is not comfortable with hurting others, but taking ships by force alone costs more lives than can be sustained. Thus the theatrics: gruesome acts of violence upon crews who choose to fight, always leaving a handful of survivors to tell the tale. Some adopt fearsome costumes, such as wearing a fake eyepatch or painted-on scars to demonstrate the many fights they've won, most speak roughly and threateningly. Some just learn the kind of silent glare that puts a chill down anyone's spine. Because the more merchants who surrender without a fight, the more profit they take without having to fight for it.

Unskilled Sailors

For most crews, the ability to sail the eight seas is considered secondary, with many volunteers learning the ropes after joining up. These crews typically only have a handful of veteran sailors: a quartermaster, a helmsman, and a few of the quartermaster's mates. Even the captain need not be professionally trained, as for privateers that role is typically one of a commander in battle. This requires a solid understanding of the ship's capabilities and thus typically being a long standing member of the crew, but not a full understanding of weathering a storm, the logistics of supply, and other such details considered essential for most captains. This, combined with a common lack of discipline, means that many tasks that are essential to a ship's long term survival just don't get done: nobody joins a pirate crew to swab the decks or muck out the bilge.

Who's Paying Us Again?

Privateers also have a nasty habit of disregarding their employer's orders. Often they follow through for a few months, usually hitting a specific ship that they were asked to attack. But before long, details of the arrangement will usually be conveniently forgotten. For the more successful crews, this usually means not attacking their employer's ships, but attacking any other target of opportunity rather than specifically those they've been paid to attack. But there are plenty of crews to whom their contract is not worth the paper it's written on, attacking any ship they think they can take on regardless.

The Exceptions

Conversely, there are a handful of privateers out there who operate with the discipline and organization of a professional navy. These typically hire a decent core of professional sailors, appointing them to train the regular crew to operate and maintain their ship properly. Similarly, they tend to keep a much closer eye on their employment contracts, as well as preferring more specific, time limited contracts, with known deadlines or even individually targeted ships.