I've tried save/quitting and alternating between all my player characters, but for some reason he hasn't gone into his house once so I can scare him for lollipops. Anyone else have this problem? Is there a solution?
I'm pretty sure that the villagers that are inside will stay inside, and the villagers that are outside will stay outside. Please don't take only my word for it, though! It just seems that way to me, since none of my villagers went inside or outside if they were already outside or inside, respectively. Again, I am not sure if this is correct, but I hope it helps!
If you're trying to go for the full creepy set with one character though, it's kinda necessary to save/quit, then start up again to reset which villagers are outside and which ones are indoors.
It doesn't really matter now since Halloween is over in my game. If anything, I'm curious if this has happened to anyone else. :/