I love betting mechanics in RPGs and you done built an entire game around them. The conflict resolution system seems very cool and I like that actions become easier the more players are willing to risk, it fits the theme well and is definitely suited to the type of fast paced, high stakes action of a one shot type game. I also love the little bits of flavour like the note about shallow water.
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Thank you! I don't have much experience with betting in RPGs, but I've been intrigued by them ever since I read Dogs in the Vineyard, and it seemed appropriate for a pirate-themed game. Fitting the bits of flavor and art in are always the most fun part of short RPGs for me (and often the most challenging, since I'm a pretty verbose writer, normally!), so I'm glad you like them :)