Here’s the idea.
The kraken, megalodon and the Skeleton ships will all be in game after the cursed sails event is over, and I think they need to have more specific purpose as boss fights. So they are set up as random events and I assume the Skeleton ships will leave their specific spots and only appear in groups of 1 or 2 at a time as a random event, but for the sake of this idea let’s say just 1.
The kraken should be buffed, and the megalodon rarer to appear but more likely to be aggressive, and the skeleton ship should have a comical bail function added where sometimes the skeleton captain will frantically panic and run from the helm and bail a bucket or two, the animation having that special rare humor to it. This wouldn’t happen if someone was on board.
This would increase the survivablity of these bosses if they made it so that the boss could retreat randomly before you can kill it similarly to how they appear.
If you pretend all of the above is true, here comes the real idea.
The kraken should use its tentacles to suck up loot from the top deck, and if it sinks a ship takes all the chests and trinkets, and the more ships that are sunk or stolen from by the kraken the larger the loot drop for whoever killed it would be.
The megalodon would get a new attack that would ram the ship to bounce players off, and any players that is killed would add a foul skull to the drop, aswell as any skulls that were on any ship that sunk, increasing the megs drop for whoever kills it.
Yep, you guessed it. The skeleton crews would be able to shoot over Skeletons who would climb the sides of the ship with an Audio cue, who would steal merchant loot and jump below the ocean and swim back to their ship at a comically fast speed. This would add to their loot drop for whoever sinks them. A way for players to produce crates of goods would enhance this and the merchant alliance as a whole.
This way each boss has a specific reason to search it out, and even if the first encounter rate is rare, once a ship engages it if the boss retreats you could go to an outpost and pay the trading company relative to that boss or maybe just the OOS person with the crystal ball, to get an approximate new location to spawn the boss. So players could hunt them for leveling purposes rather than defeating them being worth nothing, atleast in the case of the kraken and meg.
I may edit if I think of anything else or someone else has any thoughts that they want me to add that I agree with, so let me know what you think!