Very interesting analysis indeed. I agree that Aiden's angle seems so far to be the humiliation of the power figure, such as a teacher.2) Before the removal of the so-called Dylan's twist from the events of Day 18, Aiden and Dylan's stories, in the original idea of the developer, should have developed hand in hand with each other, with a mutual participation of one in the cause of the other. In fact, before this part was removed from the story's narrative, behind Aiden's blackmail was Dylan's desire to see his mother return to wearing sexy, provocative clothing as she did when she had not yet entered (to his way of thinking) a mid-life crisis. To make this fantasy come true, Dylan had contacted Aiden, the more asshole among his mother's students, who, in exchange for some mysterious computer data, had willingly accepted the assignment. In turn, Aiden, in order to justify his demands on Sophia, had covered it all up with an always valid blackmail: either you do what I ask every time I ask or I will beat your son. So Aiden's mission would be to blackmail Sophia into wearing increasingly revealing and sexy clothes according to Dylan's desire to see his mother expose more and more of her legs and cleavage at school.
I have just a minor correction to your premise, though, that doesn't change much the whole point.
Dylan was completely unaware of the tasks, the deal was just to force Sophia to dress sexier under the threat of beating his son. Even when the twist was there, the 12 tasks were just Aiden exploiting the situation to have even more fun with it.
If we go back to the script with the twist, after Dylan reveals the story to Sophia:
Python:
s "Just out of curiosity. How the other tasks would've looked like?"
dy "Um, what?"
s "There were supposed to be 12 tasks, right? Every single of them was connected with a sexy fashion style or what?"
dy "Which 12 tasks, what are you talking about?"
s "{color=#f2ff66}(Damnit! Aiden that little prick! Of course he tried to take advantage of it! Son of a bitch!)"
s "{color=#f2ff66}(How could Dylan only be so naive to trust this asshole?)"
s "Ah, nevermind."
dy "No, Mom, seriously. Which 12 tasks? What did this jerk tell you?!"
s "What does it matter now?"
dy "{size=-3}Grr! That son of a bitch!"
So Aiden didn't plan the tasks to fulfil the deal with Dylan, it was a "side project" more to have personal fun.
This doesn't change you point of Aiden trying to showing his power over the authority figure in the school. We'll see if and how this could evolve over the remaining tasks.
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