I'd suggest starting from the chapter that follows the last episode of the anime. That way, you won't miss any new developments and can continue the story smoothly. But if you want a more immersive experience, starting from the first chapter could be great too as it might give you new insights.
Well, Harry could be really confused at first. Ouran is a very different world from Hogwarts. He might be shocked by the opulence of Ouran Academy and the strange club system there. Maybe he'd try to find a way to fit in while still being true to his wizard self.
Sure. The Ouran Host Club manga has finished. It had a proper conclusion that covered all the important aspects and left a lasting impression on readers.
The Host Club members would probably be very curious. Tamaki might be the first to approach Harry, thinking he's some kind of exotic new guest. Haruhi would be more down - to - earth and might try to figure out what makes Harry so different.
I'm not sure specifically as there could be many different interpretations. It might be a fanfiction where the character Kaoru from Ouran does something that causes harm, either physically or emotionally, to another character in the Ouran universe.
A fanfic with this scenario could start with Harry arriving at Ouran Highschool on a rainy day. He has his trusty umbrella, which could be a family heirloom or a magical item. As he walks through the school grounds, the students of Ouran Highschool are intrigued by his different appearance and the old - fashioned umbrella.