I also don't like it when characters say they want to call it a day just because a convo can be triggered. To me, a natural first Long Rest should be after the Dank Crypt. Anything before that seems too soon. You barely did anything. What is that? An hour at most of the day to land on the beach, roam about, meet some people, and explore a dungeon that isn't that big. Characters shouldn't be tired and needing a rest just after facing a few mercs.

That's why I think each long rest should also be only 8 hours with 2 long rests a day. That makes more sense. I might rest 8 hours twice before the Druids grove but not 2 days.

So Raphael is a perfect example. I am currently doing a playthrough where I haven't long rested at all because I haven't needed to. Im at the druids grove. Im going to meet Nettie. So not Gale Dialogues for me. I miss them entirely because I played well and didn't End Day after playing maybe an hour.