My thoughts on the Keep:
- We have, I think, three or four people capable of creating very compelling disguises for themselves either by spell or ability. I have proficiency with a disguise kit but no actual kit.

I wanted to put an evil mustache on someone.
- If we can infiltrate all the way to Jolly, we could probably bypass a lot of fights. If Tom is right, Jolly's death might be an incentive for the bandits to flee or surrender. The more fanatical of these water guys will probably still fight, but the fights would probably be easier without the bandits taking up space. Not sure about the bugbears, maybe we could pay them to leave?
- We should probably do this after evening falls. We all have darkvision or better, so none of us would be bothered by the lack of light and it would provide disadvantage to any perception checks attempted against us by those that don't have darkvision. We should particularly try to do it after dinner so we're not trying to pull this off in the dining area filled with everyone in the Keep, LOL.
- The basic idea would be that the Shoalar was taken prisoner by the adventurers he was supposed to kill. The rowboat encountered the adventurers, resulting in a pitched battle. Only a few survivors remained, with deaths on both sides. Having been told of the prophecy, Shoalar thought it best to keep the prisoners so Jolly could interrogate them.
- At least, that's what I brewed up. Mechanically, I can probably do a pretty good job pretending to be Shoalar, assuming I can keep people from touching me (or find a change of clothes in the keelboat and shed my armor). I have Advantage on Deception checks when pretending to be someone else due to the Actor feat.