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So I’m confused lol. Does barrel leave bareshade? I’ve completed all the quests that are allowable up to this point, and I can no longer interact with barrel in the inn. I’ve yet to complete the scene where he stays with you in bareshade. Is this still doable? Or do I need to start over to achieve this?

No, he actually stays in Bareshade. And you can meet him in the Bar if you have 25 or more bandit's moral and have a love potion with you.

I’ve slept with him in the bar and completed the “get bandits supplies” quest, and then he disappeared. Not too sure why he left or how I can get him to come back. He’s been staying at the bandit camp.