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.