Kinda funny but I feel the female MC make no sense. She is a genius at business, can waste a lot of money in stupid things, yet she does nothing to improve the male MC life beyond taking him in dates. I not saying she should give him free money or anything, but she could give him or his sister easy jobs with decent pay to live a more or less normal life. And no, I don't think she is already doing it because the MC had to save even the bus money to ease their situation a little.
Anyway, this was only a one-shot so its fine for it to only focus in the premise its trying to show.
Forgive my bad english, please! I'm not a native speaker and my mind just refuse to make proper sentences right now.