I just thought of the cutest idea!

I could see this.
Once you agree to the upgrade Nook would recommend you find a place to stay (and remind you that you can access most of your stuff through the train station)
If you needed something that's inside your house you could maybe talk to a foremen who would show you a list of your house's inventory (and maybe mail) so you can grab what you need.
Talking to villagers gives you the option of asking them to let you stay the night.
If a villager agrees, when you start the game you start from their house all cheery
If you haven't found a place, you start at the City Hall and have a crik in your back.
 
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I love the idea of having sleepovers with our villagers. As mentioned, it would be a little hard for it to work, but I still love the idea. I'd love to have one with Ken. c:
 
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