This is pretty standard manga villain behavior. Average manga villains almost always seem incapable of understanding how their perfect plans could fall apart or how anyone could actually stand up to them and usually break down complaining about how things aren't supposed to be that way and it's not possible, etc. etc. Feels like it's probably a cultural thing to do with how they treat excessive pride and ego (except when the person is able to back it up, then their ego is considered a positive because they're better than everyone)
This probably worse than that.
This Pina is like someone who playing gacha games as a trend. Relying on items instead of looking up guides or trial and error.
When she works at the soup kitchen, she did mention that her rep probably going to lure in "characters". In a way, she still doesn't treat the people around her as real human but as npc.
Plus, her "political" games is only high school level combined with her commoner upbringing, she doesn't know how to "act" around nobles.
Not even once she or Willard has show to do any information gathering before making any moves, thinking what they do is "groundbreaking".
Erhashaa back handed comment to Willard also quite nasty bordering public execution in front of others.
When you are stupid, having someone stupider than you stroking your ego must be nice.
This is what he basically meant about the relationship between Willard and Pina.
