Madness is the first pillar, the one who possessed Shinra that one time through Adolla Burst. The one whose appearance is identical to Iris. From then count the order of awakening.
I don’t think it’s an arranged marriage. Hayasaka or Kaguya would have mentioned it by now. Maybe she’s going to tell him whether she got into Stanford.
Yeah, the manga follows the light novel. The web novel doesn’t go into detail about Farmus and Youma as a hero conspiracy but the light novel goes into great detail and it’s really good. Also, I’m pretty sure this meeting is LN exclusive but I could be wrong. It’s been a while since I’ve read...