Example. Player A the rigger is assigned the job of Line Work which has a DC of 10. They have ranks in [Profession (Sailor)] so they will use that skill for the check. In addition to performing their normal duties, they wish to explore the galley [A9]. They will receive a -2 penalty on the skill check to perform their job. They then roll a DC 10 [Constitution] check to determine if the work [Fatigued] them. They do not apply the -2 penalty to the [Constitution] check.
They then sneak downstairs. A successful [Passive] check reveals that there are several knives laying about, not all of them designed solely for cooking. Looking closer by making a [Perception] check, they realize that one of those knives is actually a masterwork dagger. They know that attempting any further actions will mean risking a [Stealth] check to avoid drawing the cook, Fishgut's, attention. They're really not supposed to be in the galley, so Player A returns upstairs to blend back in with the rest of their shift.
Player A decides to return the next day; they really need that knife. They are assigned the same task as the previous. They take the same [Daily Ship Action] as the previous day, as well, and the results are the same. Fishguts is still there, but he's reasonably distracted preparing for the daily meal and the cook's mate isn't present. In addition to gaining any information revealed by a second [Passive] check, Player A may attempt a single [Sleight of Hand] check against Fishgut's [Perception]. They succeed; had they failed, Fishguts would have caught them and likely turned them over to Master Scourge for punishment. However, they must make an additional [Stealth] check at a DC 15 because even though Fishguts is distracted, he's not blind. This time they fail, but not by much. Fishguts interrupts their actions, preventing them from lifting the masterwork knife but merely sending them along with a scolding for getting in the way.
On the third day, Player A returns to the galley yet again and this time is in luck because, for whatever reason, the galley is completely empty. There are still more things to discover, as another [Passive] check reveals: Player A happens to notice a small satchel of gold lodged in a corner behind a meat rack. First, they snatch up the dagger and the gold, then make another [Perception] check to look around some more. They discover that a heavy cleaver would make a pretty serviceable hatchet and snag it, as well. They get the feeling that more [Perception] checks will turn up even more useful equipment, however, doing so runs the risk of alerting Grok in the quartermaster store next door, forcing a [Stealth] check. They instead return to the top deck to finish their work.
Example. Player B has had a long day of pirating and wants nothing more than to kick back and relax. They pass on any chances to play or gamble on any pirate games or entertainments and head straight to bed, curing the [Fatigue] they had incurred during their job duties. However, they knew this was likely to be their only chance to meet with a particular member of the crew and attempt to influence them by giving them the dagger Player A had knicked a few days previous. They wake in the dead of night and head to the appointed meeting spot, but their crewmate is late in coming. Fortunately, they are successful in their [Diplomacy] check to alter the crewmate's attitude towards Player B and by extension her close cohorts. They must make a DC 14 [Constitution] check to avoid being [Fatigued] for the next shift, however, due to their interrupted rest.
When not engaged in their primary past time of looting and plundering, pirates in the Shackles can find their lives incredibly dull and monotonous. Crew members work during the day, with night time duties delegated to the officers and specially chosen mates. This leaves their nights relatively empty and free to do as they please, so long as they stick to the lower [A10] or main [A3] decks. Sailors caught outside of these areas after the "bloody hour" and gathering their meal are immediately suspect and often subjected to tense questioning, sometimes by Master Scourge himself. The exception to this is the Cook's Mate, who can travel to and from the galley [A8] more or less freely.
To wile away the hours, bored pirates have come up with a number of games and entertainments to fill their evening hours until they bed down. Most of these take place on the lower deck [A10] in the crew berth. Entertainments go on until there are no crew members awake enough (or sober enough) to continue, no matter the late hour. Officers rarely bother to break up pirate entertainments: Master Scourge would rather whip bloody any pirate too exhausted to perform their duties the next day.
Songs and Stories[Perform (DC 20)]: Sailors love free entertainment. Gambling, drinking, and contests of strength are often accompanied by crew members waxing poetic in the background. Generally, pirates enjoy songs of wealth and glory and adventure, limericks of an unsavory nature and - perhaps surprisingly- epic poetry. Players that succeed on a [Perform] check receive a +2 circumstance bonus to [Charisma] when interacting with other members of the crew, excepting officers. Additionally, songs and stories that focus on bloody battles might grant further bonuses with certain members of the crew.
Occasionally, performers misjudge their audience or abilties severely. A [Perform] check of 9 or lower results in a botched performance. In addition to being boo'd and heckled into silence, PCs must make an additional DC 15 [Bluff] or [Intimidate] check the next time they attempt to perform for the crew or they'll be ignored.
Note: While using magic to enhance a performance is possible, how you present the magic and whether that presentation is engaging enough still requires a [Perform] check to net the circumstance bonus.
Pirate Games and Gambling [Varies]: Pirates love to gamble and have come up with a number of interesting games on which to do so. PCs may engage in these contests directly or just bet on their outcomes. The minimum bet for any pirate game is 1 gp. The maximum bet any non-officer pirate might accept on any individual night is 20 gp. For simplicity sake, bets are always a 1:1 odds. Below are listed a few of the regular pirate games, though this list is non-exhaustive. Any games not detailed below will have their terms listed in the play thread.
Arm Wrestling: Unlike traditional games of arm wrestling, this contest aboard a pirate ship has a much greater chance of injury. Contestants litter the sides of their playing field with shards of shattered glass or other sharp objects. Contestants make opposing [Strength] checks; the loser suffers 1d2 + the opponent's strength modifier in damage as their arm is forced into whatever dangerous objects litter the playing field.
Hog Lob: Players use a lead ingot wrapped in piglet skin, the "hog", to play this game. They take turns hurling the hog across the main deck [A3] in an attempt to see who can throw it the furthest without throwing it overboard. Gamblers bet on the winner, as determined by who gets it the closest to the railing on a single throw. Players make attack rolls using their CMB (the hog counts as an improvised weapon unless the player has the Throw Anything feat or a similar ability.) Players may voluntarily use less than their max CMB if they choose to do so. The distance thrown is equal to the results of the CMB check (a modified 17 means that the hog is thrown 17 feet). As a reminder, the main deck is 30 feet wide; throwing the hog overboard is an automatic failure (and is bound to make the player less popular with the rest of the crew, especially the quartermaster.)
Heave: What's piracy without drinking games? Occasionally the crewmates will bust out the rum from their secret stores. Unlike other pirate games, Heave is the only contest that pays out at higher than 1:1. Any number of crewmembers may play at a time. Players agree upon a set amount (the ante), that goes into a "pot" in the middle of the table. Winner takes all. Getting caught stealing from the pot carries the punishment of keelhauling the next day. The object of Heave is simple: players drink until their opponents pass out. Each participant, in order, must drink a half-pint of rum in a single shot. Doing so forces a [Fortitude (DC 15)] save; failure increases the attribute damage dealt by their meal ration by +1. This DC increases by +3 per round. Players that fall to or below 0 [Consitution] due to this ability damage pass out and are removed from the table. The winner is the last pirate standing. Losers that drop to or below 0 wake the next day with 1 [Constitution]; ability damage is healed in the normal fashion.