Great chapter. Ugh, I want Hitsugi to win though...
I've always considered her to be the "stupid" because she most probably won't understsnd why and how people do things. It's not that regular folks can't do anything they want, they sure can, but sacrifices will be made in some way for that to happen. That's not the case for her. Consequences don't exist for her actions ( within reasonable boundaries ) and that skews her views on things.
This is completely wrong. It doesn't matter what amount of capital or inheritance you start out with, you can always make the wrong decisions and screw yourself and your company, because consequences always exist. Most businesses in real life fold within a few years, because their idea wasn't good, they didn't manage their assets correctly, bad leadership, or whatever else. Hitsugi could have just as easily screwed up somewhere along the way and lost everything, and that's not including constantly putting it all on the line via the duels.
If we want to talk about reality, and who has dealt the most with consequences, sacrifices, or what not, then, in reality, it would be Hitsugi. She's a teenager whose properly managed her inheritance and a successful school/company despite all the business, economical, political, personal, etc., problems that an organization of its scale would run into in the real world. She's like an Elon Musk + Paris Hilton in a way.
Hitsugi didn't ask to start off rich by the way, but she made the most out of it. If she had started out poor, I think she would have become rich and successful in any case, because she knows how to deal with pressure.