Same problem.
I'm having the exact same problem, with the Cutless quest. I need to get the pages of the Pirate Lore back from EITC ships for Will, and so far I've only been able to get one. Now when I sink the ships, it doesn't even bother searching for one. Is it supposed to be like this now? They don't even bother telling you if you did or did not get it?
~Sonicblur
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