Ooh Dante's Inferno layers corresponding to punch holes could be interesting, then it could get into a bit of like the Saw films where Jigsaw was watching them and gathered those he thought needed to learn a lesson and all that. So i think ur deff onto something there!
Especially thinking of the idea it mirrors The Menu with Jack either A. ruining plans, B. being one to either help the others through potential trials to come (If it ends up like Saw and they represent a different sin) or C. showing The Showmaster that there are some who can appreciate art for what it is and see it's parallels to real life.
Awesome theory crafting there. Can't wait to see what comes next :3