I have far too much fun writing events that will only occur to a miniscule fraction of players without a walkthrough.
In order to reach some of the dialog I'm writing at the moment, you need to:
1 - Have figured out how to clear your demerits so you're eligible to run for office
2 - Run for Treasurer
3 - Choose a particular assistant for your campaign
4 - Have managed to spend all your money so that you need a loan
5 - Actually win the campaign
6 - Spend all your money AGAIN so that you can't pay back the loan
But then, most ways to seriously annoy the teachers involve an unlikely series of actions. Wouldn't want players getting themselves unexpectedly expelled... So most of the time, earning demerits requires exploring off the beaten path and then making choices that you probably should have realised were a bad idea.