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Thanks for the feedback! I was watching a lot of One Piece and Our Flag Means Death and listening to a bunch of Alestorm. The bear was explicitly influenced by One Piece. He was originally planned to be Kozel "The Mad Bear" Medved, a former combat surgeon with anger management issues. However, while writing it up, I jumped the shark and just made him an actual bear. I'm considering reigning it back in and making him a former combat medic with the power to turn into an actual bear to make it feel just a touch more grounded. 

When it comes to Objectives, I'll be honest. When I first picked up Eat The Reich, I just though that was how the system worked, so hopefully it feels intuititive in play. 

I am unfortunately lacking in talent for visual artistic media, so if I didn't have free art, I wouldn't have any art at all lol. 

Lastly, I'll copy the below from another comment on ship-based combat, because that is something I'm thinking up:

I've got two ideas on my list for how to incorporate ship based combat. Both are effectively an end game chase scene. The most obvious way is that once the players have Maggoteye's head, they need to get their ship out of the harbor and have to escape other ships chasing them. The other, which feels more piratey is that when they find the governor, he tells them Maggoteye's head is on a ship headed somewhere and then they have to get back to theirs, hunt the ship down down, board it, and find the head. I would just need to slim down major/minor objectives along the way so it doesn't feel too long.