Damn, quite a setup to put Iruma and co. in a lose-lose situation. Shiida sensei caught feelings and got scorched for it by the evil demons sp fast. Those evil demons of origin really suck. And I guess we should have saw this coming since we know Shiida sensei is technically a "double-agent".
But this chapter marks the start of what will likely be a new war amongst the demons... If one has been paying attention, one should know Iruma will become the next demon lord by prophecy from all the previous foreshadowing... and the next generation of 13 crowns will likely all be from the misfits class.
The major factions/players we have seen thus far in the story are Baal/Origin demons, the 3 greats, and the (soon-to-be-divided) 13 crowns (including the border patrol orgs that have 2 or 3 people seated on there). The wild cards we know at the moment are: Alikured, Derkilas, the angels/heavenly realm, and likely Kirio (the former club senpai I remember right).
Ole Henri might be suffering the most here, because I get the feeling that he will be putting himself out there the most to get his daughter's BF to stay cause he ain't gonna let them go through what he went through with his romanticism powers.