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.
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.
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.
I'm not very familiar with this specific fanfiction. However, in general, pregnancy fanfictions often explore new aspects of character relationships. It might delve into how Haruhi and Kyoya handle the unexpected situation, and how it impacts their relationship within the Ouran High School Host Club setting.