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Thanks for the feedback. Im really happy with the concept of the flaws but definitely think some of them could be more refined. One of those things that I think has a lot of promise but I need to spend more time cooking them up for each character. 

The bear character is absolutely out of left field and is still pretty half baked. He was originally intended to be a human medic with an old war nickname "Mad Bear". But I was watching a lot of One Piece while working late at night and I think a little too much of that influence worked it's way in. I was in a rush to get him added and probably could have left him out entirely until I had a better idea of who he is.

I had the same thought about omens and almost dropped it entirely for that reason. I couldn't think of a suitable replacement to keep the pattern going. But I felt like the thematic influence of having the concept included outweighed my concerns about it not fitting perfectly with the other four.

It's funny you say that the adventure needs more time on ships because my initial outline had a fourth phase which was getting the boat out of the harbor. I cut it for time but I agree that it does feel like the pirate adventure needs to at least be partially spent on a boat.