Bad Accident - Gm decides what happened, but the random npc is dying from the accident. DC 15+APL heal check or the pirate dies.
Bad Weather - A particularly bad patch of weather plagues the area. There’s a 10% chance the weather is devastating. Attempt a DC 20 Survival check. If you succeed, you’ve anticipated the weather and your ship makes it without damage. If you fail, the bad weather damages some of your supplies, and you lose 1d4 points of Goods. If the bad weather is devastating, make a DC 25 survival check. If you pass you loose 1d4 points of goods. If you fail you loose 1d3 plunder and there is a 25% chance a random pirate is lost at sea. Sometimes weather lasts for days. There is a 45% chance of another day of bad weather, this is -5% cumulative for each additional day. Bad weather sailor checks: -5 on pass, -10 on fail. Devastating: -10 on pass, -20 on fail. Cumulative -2 to sailor checks for each day of bad weather.
Brawl - An all out fight between dozens of pirates has started on board, DC 20 intimidate or 1d3 plunder is destroyed.
Burglary - Someone has stolen some potions, scrolls or other magical goods. DC 25 spellcheck. Pass - your magical defenses stopped the culprit (random pirate). Fail - 1d6 random scrolls, potions, or minor items are stolen.
Contamination - Something gets in the food causing you to get rid of 1d100 % of your rations.
Day of Rest - it's a beautiful day and nothing bad happens, everyone is in good spirits +3 Sailor Checks.
Drinking contest - 2d6 pirates decide to have a (rum rules) drinking contest.
Duel - Two sailors have a dispute that must be settled with a duel to the death. You can prevent the duel succeeding at a DC 25 Diplomacy or Intimidate check. Otherwise, you lose a sailor and -1 Moral.
Entertainment Ship - a ship is on the horizon, as you get closer you see a white flag raised. The ship turns out to be traveling entertainment who makes money off of other traveling ships. This ship may be a traveling brothel, a restaurant, a theatre, or something similar. Regardless the crew takes the rest of the day off to enjoy the entertainment. +1 moral. -1 moral if the Captain declines the entertainment.
Escaped Animal - Be it one being trained, transported, or used for food. DC 20 Handel animal to round it up before it does damage, or create an encounter to deal with it. Each failed attempt is -1d6 loss of goods.
Explosion - Crafting goes awry or dangerous regents are spilled. 50% chance of a major explosion (1d6 dead, 1d6 plunder destroyed, 1d7 days to fix the ship), 50% minor (3d6 goods lost).
Festival/Holiday - today is a special day and the crew doesn't expect to work. Force them to work - Diplomacy or Intimidate DC 30. -1 Moral and additional 1 for every 5 under and they work. Or don't make them work.
Fire - somehow a fire breaks out in your storage area. 75% chance of a minor fire destroying 1d10 goods. 25% chance of a major fire doing 2d6 worth of plunder damage. Or create an encounter to put the fire out, dealing damage to npcs, plunder, and ship based on your discretion.
Food/water shortage - miss calculation of food supplies, you must make an emergency dock to replenish storage. Cook makes a DC 20 survival check per day to catch enough fish to satisfy hunger. -1 moral and -15 on sailor checks for each failed. -2 cumulative to sailor checks per day regardless of survival save. Take a day at dock for each lost moral to feast, restock, and rest.
Friendly Competition - Something sparks a crew wide competition. (Climbing the rigging, setting the masts etc) +1 moral.
Good Fortune - For 7 days gain +4 on Sailor Checks
Grand Feast - the cook made an incredible meal (slaughtered an animal, caught a rare fish etc) +5 on sailor checks, +1 moral
Hazing gone wrong - a random new pirate is maimed or dead after hazing, no one speaks up about who the suspects are. Leave it be or flesh out an investigation.
Hearts Desire - Two of your crew are in love and ask permission to take leave for a marriage and honeymoon. If denied -1 moral.
Infestation - Spiders in the bilges, rats everywhere, stirges attack, sharks surround the ship, whatever the infestation is, it's keeping the crew on edge. DC 20 Handel animal to take care of it. -5 sailor checks and -1 to moral until the infestation is done. +1 to the Handel animal DC (max 30) for each day it lasts.
Infighting - ship politics are getting the best of the pirates. This last for 2d6 days unless you make a DC 25 bluff, intimidate, or sense motive check per day. This must be passed 3 times. Until then loose 2d6 to sailor checks per day due to arguments, and fights breaking out during the day.
Jester fun - whoever took Owlbears spot is brought out for entertainment +1 Moral
Lazy Worker - you catch a random pirate sleeping on the job, or being extra lazy and must deal with it.
Mutiny - a random npc challenges for an officer position. One on one duel for the spot.
Mysterious item found - an item is found in some overlooked plunder DC 30 spellcheck to know what it is, fail finds traces of a curse on the item. Create item at your discretion.
Outbreak - Something is making the crew sick. -5 sailor checks until Heal DC 30 is made.
Prosperity - the pirates are happy. For 1d6 days gain +5 on sailor checks.
Quitter - a random pirate (including officer) finds that this is not the life for them or they want to retire. DC 25 intimidate to gang press them back to work (-1 moral because others feel like they are being forced to work) or release them at the next stop (+1 to moral).
Rivalry - the crew comes to an agreement that they don't like the way the captain is running the ship. They choose a random officer to take his place, forcing a rivalry. If the Captain won't step down he/she must pay them off with 1d6 +4 plunder, a DC 25 diplomacy, or a DC 25 intimidate to gain his trust back. Each day of a failed attempt they demand +1 additional plunder. -5 cumulative to sail checks each day of failure or non payment. If plunder is not available the captain is forced to make the checks or step down.
Robbery - the Quartermaster store was robbed, DC 20 intimidate to find a random pirate with the goods, if failed 1d6 +3 goods are lost.
Rumormongering - Rumors are being spread about an officer. That officer must make a DC 20 diplomacy check to spin the rumor into their favor. Pass +1 moral, fail -1 moral.
Scandal - Some sort of scandal strikes your ship - an affair between an officer and pirate, a destructive prank or dangerous hazing, or the like. The scandal’s repercussions last 2d4 days. During that period, it’s difficult for the crew to stay busy, it takes a –5 penalty on sailor checks. Once per day, you can attempt to repair the damage to your reputation and end the event with a successful DC 20 Bluff or Diplomacy check. Failure extends the duration of the scandal’s fallout by another 1d4 days.
Sickness - A flue/fever is going around. -2d8 sailor checks for 2d6 days or DC 20 heal check to get it under control.
Small ship problem - there is a small leak, a rudder snapped, broken bilge pump, etc. that needs repaired. -2 to sailor checks until it's fixed. To bad what you need is not on board. There is a 5% cumulative chance per day that it gets larger and causes an additional -2 to sailor checks. The ship must make an emergency dock for 1d4 days to fix it.
Spoiled Pirate - a random pirate thinks he deserves more than what he's getting, he demands a 3% raise or causes a ruckus. No matter what you say he secretly complains giving the crew a -1 moral.
Sweaty Pox - Some sort of pox is spreading, it last for 2d8 days. -5 on sailor checks, 20% chance per day that it's -10 due to more pirates being sick. DC 25 heal check per day to stop the infection.
Unstable Mutagen - an alchemical mishap has caused a distraction. -5 on Sail Checks for the day.
Uprising - swabs want new jobs or they are going on "strike". -5 on sailor checks until it's figured out (higher pay, switch up half the workers jobs, DC 30 diplo or intimidate check).
Violence - 60% chance this is just a simple fight between 2 pirates, requiring a DC 20 diplomacy or intimidate check to relinquish. 40% chance that it is a violent attack requiring intervention.
Weather in your Favor - +10 Sailor Checks
Wild Night - your pirates partied a little hard last night causing destruction of 1d3 plunder and a -2d10 to sailor checks due to hangovers and soreness.