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At what point is a quest overburdened by rules? Trying to find that sweet spot between minimalist/simple and making the game my own! 

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As a friendly Quest Jam competitor, I suggest looking at last year's winning quest and compare the complexity of their entry to yours (psst last years winner is also a judge this year).  The competition is to create a cool quest.  I believe you can create a cool interesting and most importantly fun quest without reinventing every hero class.

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Thanks for the tip! I am proud of my Pirates. As long as they get some playtesting from someone other than myself, I will consider myself a winner!