Update: went back to an older save, played through again after finishing Sauce/Off and Touched by an Angel, and this time Paint the Town messed up the progression of In for a Dollar. Same issue basically, but with the women's bathroom not giving a quest-related interaction. Still stuck at 7AM in the dark school. Going to load another old save and try and finish every 7PM quest before Paint the Town triggers, but this is a really annoying bug :( Love the game, though.