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Thanks guys.
To those who're also at a loss:
You can buy sleeping powder from the Merchant at the Tavern at night.
Which you can use to put the guard infront of the house of the Harvest Princess to sleep.
You have to get your kingdom affinity higher with the princess before they give you the next part of the quest. She'll put a pumpkin on your head (It's a costume equip for the knight) allowing you to get past them during night.
Ah thank you~!
Status Update: I just needed to boost kingdom affinity a bit more to continue the next part of the quest, AND it turns out it is one big quest as opposed to several little ones like I initially anticipated...