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Sometimes they just don't ask.
I've only had to get Jack his thimble twice. It seems I always have to get his book.
Dutch didn't ask for his pipe last time, but he did this time. Hosea always gets his book.
It's not a bug, it's just random and time sensitive. There are certain moments, after something else has happened, or hasn't happened, they'll ask. If whatever has to happen hasn't, they won't.
Most happen in Chapter 2, but after Chapter 3 they never happen.
I had this happen to me on console after multiple playthroughs, one of which I 100% completed, with the saves still there. The issue is caused by older savegame(s) from my personal experience. Removing any other data didn't work for me there. It may be one save that's the culprit, it may be several, you won't know until you temporarily remove older ones. Considering you're on PC this will be a lot easier than on console. I didn't want to deal with the hassle of swapping out saves on there, so I created a second user profile on the console instead for my fresh Red Dead playthrough which also did the trick.
Your savegames on PC can be found here:
Documents > Rockstar Games > Red Dead Redemption 2 > Profiles > (folder with numbers and letters).
This thread down below is what confirmed the problem for me back then:
https://gtaforums.com/topic/928857-missing-dialogue-please-help-if-possible/#comment-1070738777
If you are replaying the game with older saves still there and you end up removing those it's likely to be fixed during future playthroughs, but I'm not sure if it'll also fix your recent playthrough as I haven't tested that myself. May be something to keep in mind. Normally I'd suggest restarting in that case, but that's not worth it considering you're already in Ch. 4.
Data such as Compendium and Challenge progression is part of its respective savegames. As long as you back-up your saves nothing will be permanently lost. Any temporary data you decide to delete apart from your saves will not affect your in-game progression.
https://gamerant.com/red-dead-redemption-2-companion-item-request-guide/
But I'm afraid my saves are beyond fixing. I did as you said, but nothing seems to have changed. Of course, none of the save files in the directory you mentioned are labeled so I had to guess. I also on a hunch stopped overwriting saves and just made a new one and deleted the old one instead. Unfortunately nothing I do seems to be working.
I think I'm done with this game. Yes, I know, it's childish and dumb to quit because of such a problem, but I played this game several times already, and if my, I dunno, third? Fourth playthrough? If it won't work properly, then yes, I'm rage quitting.
Still, I appresciate the help. And who knows? Maybe if I rage quit, then suddenl a solution will be found. Murphy's law always worked like this, maybe if I manipulate it, things will work better for once.
Lastly, on a side note, checking if the issue still persists can be done as early as Ch. 1 right after you rescue Sadie Adler. When the game skips to Colter afterwards and you need to decide which mission to do next almost everyone in camp has special dialogue, most of which will not trigger with this problem still active. To see if it's still present I'd recommend talking to Hosea and Sadie first. Arthur and Hosea should discuss the Blackwater robbery, and Arthur should comfort Sadie upon greeting her. Abigail should also have special dialogue regarding John's state which is easy to check while you're in that cabin for Sadie anyway. If neither of these trigger, or not all of them, the problem is not solved yet.
I hope you'll have a much better experience if you do end up returning to the game for a new playthrough someday.
Misread, edit: I've definitely gotten an item request in chapter 4. It was Lenny's pocketwatch.