Slug; the quest never reset for me for entering a village. Specifically, the quest will reset if your character in training does one of two things: 1) Enters a Temple or 2) enters the Bushi Dojo. Other than that, you can run through any town with impunity during the two day waiting period.
What resets the quest is if any quest-giver NPC reminds the character that the quest is incomplete.
-Sazerac
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