Funny to read and well written.
I am wondering how you are going to keep Harry inside Hogwarts for the next years?
If he really is that cynical, then he won't care that much for Daphne or Zacharias and he could just research other schools to go to. That would mean that Harry would be gone after first year to another school...
Keeping him there would mess with his character since he wouldn't care enough to stay there. You could force him, but he would just keep studying for himself and then flunk all classes while creating as much mayhem as possible. That and he has a contact for the papers so forcing him is basically out the window...
While I see your point, Harry's character isn't so 2-D as being just cyncial. He's also incredibly lazy when it suits him to be so. As such leaving Hogwarts and going to another school doesn't interest him because 1)It'd take too much work and he has no reason to believe that other magical schools would be any better than Hogwarts and 2) At Hogwarts he has the upper hand because of his fame and his connection to the media. In the end it better suits his needs to stay had Hogwarts, even if he doesn't like the school. More about his movites will be explained as the story goes on.