I believe the key factor of the entire Hannah's plot is by having her influenced by MC enough to gain the courage to say no to her father and write her own destiny, instead of following Allison's plan.
I also have a hard time believe Reginald is a genuine man as he presented, I mean, being the head of a founding family is basically the centre of all political shitshow. either he really don't know about MC's identity and friendly enough (as a family head btw) to bother showing a new-met-boyfriend-of-an-unimportant-low-ranking-niece the kitchen, or it's just a part of an act. (I'm just think he's sus, 50-50 tho, he could swing either way)
If that were the case, why not tell his wife to not be a total bitch? Easily the worst attitude in the entire event.
Maybe to tell him "I want my daughter to be a better person, but she can't with her mother's influence. Please take her."?
Either way, someone nice that doesn't care about power but ending up inhreeting it isn't that odd of a trope.
Btw, I find hilarious we're discussing how 3 of the girls that are basically princesses would cut ties with their families and ruin their plans (except with Regi if we follow my logic) lol
Also, I didn't note this before, but I liked how the headmistress went about earning the MC's trust, giving him blackmail to ruin her public life.
Like, damn, she's going all in for this, and with a good excuse for a sex scene with her.
AND THE MC STILL DOESN'T BUDGE.
Love this man.