If Mrfuji is right when he said that it's not impossible to tie dialogs to short rests, I agree with Ragna that it's VERY complicated (he also wrote "impossible" but whatever).
Larian handcraft all dialogs. You can see it in exemple when there is a yellow ! uppon Wyll's head in a mini camp.
When you talk to him, Wyll is not exactly at the same position he was before and the light is a bit different. This mean than one artist at Larian had created this scene entirely.
Is that a good way of doing things ? I absolutely don't think so, but that's how it works and it means that it would be very complicated to tie companions dialogs to "anywhere in the world".
But there's a very limited number of dialogs that triggered as soon as you enter the camp. All others are triggered when you click the NPCs with the yellow !
It shouldnt be too complicated to allow 1 "auto dialog" from the "auto dialog queue" per long rest + 1 "! dialog" per character per long rest if those dialogs are unlocked.
The camp would feel more alive, and the game wouldn't "force" you anymore to long rest very often not to miss content.
On top of that with 1 or 2 "dialogues queue" they could also probably untie dialogs from mini camps, which is important for my "how to improve the resting system" suggestion
