Like I suppose you could understand him talking about 'they don't like groups of men, I know' as meaning outlaws, or even interracial friendships, but given the context of this side quest I think it's not either of those things
i feel like we as a community really overlook how traumatic chapter 5 was for everyone involved. the shipwreck, arthur almost drowning and near dying, javier being shot and captured in the midst of a mad dash away from the cuban military, arthur being drugged, kidnapped, and tortured for information, javier being tortured to the point of passing out, all of them fending off a war ship and then attempting to escape an island despite fussar and the cuban military's best attempt to prevent it. i understand they're outlaws who have been in life threatening positions before, hell this isn't arthur's first rodeo where torture's concerned, but it all just feels like a LOT to manage with how condensed the timeline is for that chapter. and then they return and immediately the pinkertons are in their ass??? idk guys it's a LOT.
What I find a bit frustrating is just how much of the lore was irretrievably lost from RDR2 with several game mechanics and activities being cut from the final release.
The following audio bits can still be found in the game's files tagged as GREET_DUTCH_CHESS. Apparently, Dutch was supposed to be a rather avid chess player and, for whatever reason, there are recordings of Charles playing with him. At the same time, there's nothing left of this in Dutch's audio recordings, so it's only Hosea and Charles that still have those.