I agree on that part, the gameplay loop as it is would not have supported something like punishments mid-day. You'd have to have an entirely different gameplay loop, really, and just generally have longer days. Simple is best, as far as this is concerned, and a lot of things, honestly. Although I do think those after-hours coaching sessions could definitely work as a mechanic! Maybe you'd get points on a character-by-character basis instead of just having one counter.
One thought that I had while playing, and I hesitate to even call this a suggestion, was that, what if the outfit changes happened based on what infractions you let slide? If that inspires you in any way, it has served its purpose.
As much as I'd love to see more of this, I do get that lack of motivation thing. But if it gives you any motivation, know that I will be eagerly awaiting any updates that may or may not come to this game. Or perhaps you could make another similar game using this game's mechanics as a baseline, but with a different story, setting, and/or characters, if that helps motivate you? Like... an office setting, or a medieval fantasy army (maybe the king/court wizard found an artifact that makes soldiers become more protected the more skin they expose or something silly like that)