I'm having a hard time figuring out what causes it, but I've reset twice already after just starting over. First time Sarena ended up getting stuck on level 0. Second time Emma got stuck on level 1. I think there's a problem where if 2 girls are trying to do the same thing at the same time, the event won't trigger again. For instance, if you need a night sequence, but 2 characters are trying to appear, only 1 triggers, and the other isn't prompted to repeat
I like that you added the "?", but I wish you still showed the goals in the girls screen so I could see clearly if the quest was broken or not