I think it's pretty obvious where this disciplinary committee dude subplot is going to go -- he's gonna have the homo-hots for crossdressing Kobayashi-san.
Kinda hoping this doesn't go the Disciplinary Guy attracted to Kei route but instead does something like having them already know each other and be best bros or something and have Disciplinary Guy be like "Oh it's just you" and decide he can't be bothered with it.