I just don't like how the MC's personality has been evolving. He's becoming more and more amateurish over time. Shares way too much information with civilians, can't figure out the dynamics of the school (even though when he first showed up he wasn't struggling at all), more and more mental breakdowns. He's also doing things that don't suit his hard personality, like effusively praising some of the women or just being very open about his feelings. In general, he spends a lot of time asking for cooperation when it feels he could have just demanded it with the force of his personality. Someone like him would be very aware of the effect he has on people.
You've already presented him to us as a hardnosed, street smart, capable person so making him so bumbling and clueless now feels like unexplained regression.