Thanks for your thoughts - you can quickly skip past dialogue you've seen previously by holding X, but the plan has always been to make the school day more interesting as we go. A few new events are added each update. Remember this is still an early access game.
So if I'm understanding correctly you're on the Down with the Bad Girls quest, you've returned to Isabelle and seen the security tape, and it's said "go to school" but nothing is triggering in school, is that right? If so, I may need to see the save file to figure out what's happened there, as Poppy is supposed to ambush you again as you leave at the end of the day.
You can get the 100 credits by agreeing to sleep with Emily. After you've done that, you can return to her up to once per day to clean her house again for another 20 credits. You can also now make money by wrestling Nissa at the Pussy Pit.