Not really as "stupid" as you think, Pirate Mikeyy. It would just be an amazingly complex and time-consuming study. There are SO many variables that go into each and every "kill" that it would take an entire university research team to do the work.
Think about it... Your level versus the monster's level. Is the enemy human, un-dead, or animal? Time of day both in-game and real world. Location, number of people in party, their individual statistics, the weapons being used, the weapon statistics, the type of weapon and whether they were purchased, earned or found. Might even want to look at quests started and finished, clothing, how long the battle lasts, or even the kind of boats the pirate has. Does wearing a hat matter? Or is it the server? Or the tattoos the pirate wears or the jewelry. Male or female? Does a pirate stand a better chance if he or she has all their treasures or none of them? Am I missing anything?
I guess that what I am saying is that the rare drops are either totally random or based on a specific set of occurrences. Either way, you won't be able to figure it out and it certainly won't be as silly as "Sleep next to Darkhart for 24 hours, wake up, attack him and kill him in exactly 37.8 seconds using only a spork found in a north trash bin from a Taco Pirate restaurant while humming Yo Ho Ho and a Bottle of Rum."
The thrill should be in the hunt.