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Why not have it SET in ancient history?  like have Pope Gregory XIII (guy who introduced the Gregorian calendar) pose the questions.  that way, it has a historical FEEL, but is teaching real world uses.  that would fulfill the requirements I believe  (Note: I am NOT a judge, but interpreting the rules)

It would be tricky to fit the mechanical feel I had in mind into a historical setting, I think. It's fine, I don't need a game jam. It just seemed like it might be a good excuse to make this thing now.

Thanks,

--Josh