This is another in the series of "wanted" posters that can be found within a campaign setting.
-Yet another way for a player to be proud of being an adventurer and a way to earn some "free" gold. Things that could go wrong include: the painter is evil and is able to control people through his paintings (having a stable of adventurers to do his bidding unknown is a huge plus for evil), the painter falls in love with one of the subjects, the painter is behind in her "protection money", this is a means to make a list of all the adventurers in town.
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