Why doesn't he just check his affection points. more often. Maybe increasing charm had some kind of positive or negative affect.
Maybe Hikami views beauty as ugly, because she was told she was ugly all her life even tho she's obviously beautiful. So when she told the guy ''He may look like this, but he is an excellent man", it's because he made himself uglier in her eyes even though he actually looks cuter.
And why doesn't he just buy teh sword upgrade. It's not like he'll spend the money on anything else during the mission, as he never does. He'll get another 50-100 million after the mission is over anyway. And I don't remember loading costing that much.