As far as Hedwid dying I think that Ron or Hermione's death would grieve Harry far worse than that of an owl. I don't believe that her death would destroy Harry. She is after all only an animal and her death compared to that of Sirius or Harry's parents is nothing.
Unless of course you were just kidding around. I wonder if maybe he is going to have to give up quidditch. If he is to defeat Voldemort then it stands to reason that he would have to take deuling lessons. That's going to take up alot of time from Harry's schedule. Maybe too much time for him to be playing quidditch. Maybe Umbridge's "lifelong ban" on his playing quidditch was JKR's sybolic way of telling us that Harry's Quidditch playing days are no more.

I don't know. What do you think? <_<