A. "His methods don't defeat the premise." Lmao. This explains everything. You know what being dumb means? It means doing the same thing over and over again expecting different results. He had already an advantage and he knows what he has to improve, but in the end did worse than his previous run. You call that smart? What a joke. He's already on his path to failing, and you must dumb to think that he's not. Character doesn't equate to reputation, which the author seems to have mixed up.
B. That's not the point. It doesn't matter if the teacher or the system punishes him. The fact that he does what he does knowing it will end in the same result means he's just wasting his time.
Of course, any person can judge something he observes and that includes moral judgment. If you think what he's doing is not evil, you have a real problem. Even a serial killer knows what is evil and what is not. Try learning the alignments in dnd and you'll know what tantamounts to evil.
C. Lol, suddenly making a disclaimer and playing the victim? Don't be full of shit. The way you worded it is throwing an insult. Lmao. I'm not a fan of isekai or harem genre.