So in my first playthrough I hardly used long rest, and then when I did use it I realized you were supposed to go there fairly often to get your companions to actually talk about the questlines. Why not have it indicate they want to say that stuff during the day as it happens? It makes for some weird timing for the conversations as is. Imagine my surprise when Shadowheart is still pretty chuffed about finding the goblin priestess after we killed all of the little twerps in the abandoned village together (...felt like my intentions were pretty clear SH).

Obviously some things make sense for the camp - Asterion's reveal comes to mind - but most of the things they're saying could be tied into the game as you're running about. If all 3 companions have something to say at a given point then please show the little yellow mark, and let me talk to all (or none) of them about it. Gale can cheer my name for saving a goblin prisoner, Shadowheart can tell me she inexplicably trusts a random goblin priestess and Lae'zel can tell me it's a waste of time all right then and there. And if you want to ignore it, then have them say it at the camp later.

As the game is currently I feel a little punished or like I could be missing something for not clicking long rest often, even when I don't need to use it.

This is a good point, and a good improvement suggestion. +1

Shadowheart keep advising me talking with Gut even after I gutted priestess and other gobbos there. I'm still suprised companions don't remind me constantly that wolves hunt in pack!