If it's backwards, you can TT to real time (ie, game says 18th and you TT to 14th), they usually plant their houses next 'day'.
Look up the 'new villager plot reset trick' if you're worried about where he'll put his house.
I usually don't, but my towns are all pretty disorganized.
EDIT: I have to go, about to head offline. Great meeting/chatting with you. There are probably answers to your questions in the New Leaf subforum.