As soon as I figured out the structure of your story, it was fun to look at the character named at the beginning of each "Year" and then be on the lookout for how you captured his or her voice. You did a good job in that, both in the character's dialogue and word choices, and in the types of things that each character focused on and thought about. It was hard to choose my favorite of them all, but i finally settled on the piece about Sirius Black; you depicted his character well.
Yes, it's discouraging to discover that you've gone over the word limit and are forced to tighten up the sentences, word by word, hoping that you'll reach your goal before you have to start excising entire sentences. *sympathy*
Thanks for writing. It was enjoyable to read.