I'm not a Jew, but I'm of the Messianic variety of Christianity, and admire many Jewish traditions. Sukkot is one of my favorite, because I personally understand what it feels like to wander about.
It's a celebration of the tents while the Jews were wandering in the wilderness. And it calls to mind that God said when asked to build a temple for him, "Did I ask for a house...?" Sukkot is to regard such visitors as though God himself has decided to visit the tent, which is something that happened in the story of Lot and possibly the story of wrestling with God (Israel). So, yeah, the only way this seems kosher is if the tent/booth thing had a door of some sort, and the door was closed due to being occupied.