Not sure how bugged this is, but this is the events that happened to me with this starting a new game trying slave/pet route:
The first event about laying on the floor is as soon as I give her the maid outfit and go to the kitchen the first time
My event to lift the skirt was at 2000 while she was suppose to be doing homework, not at 1600. I get to redo the getting her to come to the living room(either 1600 or 2000), and if I choose to let her clean (reducing confidence and increasing lust) at some point it will either crash the game back to main menu, or go to the map back to before I did the event again.
Then, I can't seem to get to the point of choosing to go pet or slave. I am on part 3 where it says to get a broom (which I have gave to her) and laying on the floor again (which I never get to do). I just get the same thing about the floor either to lower her confidence or say it is sparkling.
But either way, I can't seem to progress the game on that path either way. Current stats are 114/10/55