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Love it so far but I have some questions regarding Bella and Cindy. I've checked their hints and it still says the same thing. I have Cindy near 50 affection with no change

Cindy probably shouldn't even have a hint, and Bella's hint doesn't ever change... I should really fix those. If you've seen two different bar events for Bella, you've seen it all. And as for Cindy, if her affection and corruption are high enough and you take a girl out for coffee, she might interrupt you. In there, you'll see easily if you've unlocked it all or not.

I have one last question the teacher's hint says to enjoy their time as headmaster despite the fact i've completed the content undrer each girl's hints

Yeah, that just means you've got no more main story content, so you can just do whatever else you want for now.