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What are the requirements that need to be met for the Caleb glory hole scene? and if met how do you activate it?

Also I'm having some trouble with the Northcrest's conspiracy questline, Everett doesn't have a dialogue option to talk about the orcs and neither of his other dialogue options seem to count for the quest

The glory hole scene is rng (random) when visiting Caleb. I think it happens after you get enough like with him. Or after seeing Rose talking to him.

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For Caleb glory hole scene you need to get enough likes with him and talk with Bernard at his home at night about pursuing Caleb. The option to talk with Bernard will open after having a conversation with Caleb about his friendship with Bernard. For Northcrest's conspiracy you first need to save the orc in the succubus cave(it's in the same area as Feliar's home) and talk with him, after that a dialogue option will open with Everett that will progress Northcrest questline.