Heh, I liked this. Good job with young Ash (...although I thought he and Gary were supposedly friends until they started training?), and very good realism with the school counselor. It's a shame they're all so incompetent, but that's the truth of the matter.

I think that some of your word choices could have been made a bit better, though. Here's a prime example of the sort of thing I'm talking about:

But twenty three year old Hannah did not try to pay attention on her surroundings, but to the scrawny boy in front of her.

Notice how you use the same word ("but") multiple times in close proximity with each other? That's not a good thing. You should try to maintain variety in your words, or else your readers will get somewhat bored seeing the same vocabulary repeatedly. Also, make sure you have commas where you need them to break up the flow of the sentence. For instance, look at this sentence:

Because of the fact he had to be patient, he could not of course.

There should be a comma here before "of course", since that is merely a closing remark. The sentence is currently in a format where it usually has a different meaning. Think of what it would look like if you replaced "of course" with some verb, such as "eat", for instance. That would say, Because of the fact he had to be patient, he could not eat. This obviously says that he could not perform the action "eat", since he had to be patient. If you look at it that way with the previous word choices, it says that Ash couldn't perform the action "of course", since he had to be patient. And it's clear that "of course" is not a verb. Thus, the format of the sentence currently should have that last bit as a verb, rather than a closing comment.

(...Sorry if that was overly complex, but I'm having trouble figuring out a good way to explain it online.)

But this is really good. Nice hidden emotions for Ash, and way to introduce a new character with her own problems, as well. The contrasting descriptions of the room and Ash's longing to be in the outdoors really helped, as well. This explains a lot of Ash's character, as well as how he decided to train Pokemon. You delved into the mind of a seven-year-old very well, too. Good job here. I look forward to your next piece!


P.S. You know, this could actually be continued, if you wanted to advance the plot...