Since everyone is different, and not every person is as able to pick up on patterns or disparate threads, I could see this as an opportunity to mix experience with a little bit of a record system for players to review things that they have discovered.
For instance, the information could be handled in a way where doing specific things adds the information to your Ledger (see a menu tab or even an in game book your Pirate can pull out). So, say after a Pirate kills a Plant Skeleton with a Sword it might record something about how that is a more effective way to deal with those particular enemies. Reading the various journals and books around the world could allow for information to be loaded into this as well.
It could even be handled in a dynamic manner, where things can be back filled. So for instance you might unlock Part 3 of an entry first, which is added in, and then later unlock Part 4 which amends the information in your Ledger with a new part that follows Part 3. Then you unlock Part 1 which again fills in (but this time slotting the information in before Part 3 as opposed to after it). Next you unlock Part 2 which slots into the Ledger between Parts 1 and 3. So it fills in naturally for each individual Pirate and slowly starts filling in blanks.
Other games have done this, Dragon Age Origins Codex comes to mind where bits would fill in based on when you encountered different things and events. So something might not make a ton of sense at first but becomes more clear with time. Red Dead Redemption 2 also did similar with the whole process of interacting with Animals in different ways providing additional useful details in the Journal section in whatever order you did them in.
This could range from Lore to effective ways to deal with different threats (the ways of dealing with threats and their weaknesses and defenses could again be triggered by experience based situations where once you have done something it spells it out for you in this area). It would make a handy game reference system that would benefit both players who have a harder time connecting all these dots (essentially an Accessibility feature for this group), as well as players who might step away from the game for a period of time and eventually come back (as a memory refresher).
All in all I think this is a pretty good idea that, if implemented correctly, could be a very big benefit for a large sunset of players and make the world of the game spring to life a little bit more. In my own experience I forget little details about the game all the time because it isn't a too priority for me to have that information locked into my memory, but I wouldn't mind revisiting it from time to time either without having to jump through a bunch of hoops to do so.