Oh, that's some good stuff! I didn't know that!
I'll definitely consider going back into Skulduggery now, just to get those little prompts on the street, I'd love to see it!
Yah, I was looking into that second option, too, when I was afraid of Leighton and didn't think I could skip detention, while on my first play through (My idiot good girl submissiveness was unintentionally bleeding into the game

), I did want to set up Leighton, so I wouldn't have to deal with detention, but I seem to have trouble fighting multiple people at this point (going for the unsociable[?] feat is proving arduous, and I'm getting about three students trying to gang-bang me around every corner), and I hear that's a thing you got to watch out for when messing with the principal.
First time playing, I tried to take on Bailey, and they kicked my ass in two turns, so I'm setting them as a goal of fitness for my character; if she can take down Bailey, then I'd be ready to take down anyone, I feel.
I'm sure when this game gets finished, we might seem some stronger consequence for messing with the police, skipping detention, and what have you, but as it is now, I think I wouldn't mind ruining my reputation with crime and delinquency; for that Bad Girl Hooligan run.