you are right the game IS fun but when you get stuck its boring idk what to do with maxine
There are quite a few triggers for that scene. You need to have spied on Rachel's room after spanking her in your office. You need to spy on Cassandra's room after spanking her in your office. You need to spy on Amy's room after spanking her in her office. You need to have resolved Maxine's weekend protests (by advancing Debbie's storyline). Then spy on Rachel's room again to trigger the scene. Or if you are really stuck you can trigger it by going into the cheat menu.
Apparently, it seems that Cassandra was the lynchpin, I did only public punishments, because she was flagged as "not ready to level up", after checking the cheat menu for hints I spanked her, then spied on Debbie in the evening, that opened up further progression.
But dammit, having to check the cheat menu for hints shouldn't be the way to go, there should be a better option in the flagging imho.