This is how your story read to me: Hope and Despair are "roommates" in Soul and don't get along too well. When Hope gets company, Despair hides in the basement and leaves the two of them alone to chat. However, when Despair has company, Hope runs them off after a short while. Then, Hope has some visitors who basically annoy Despair into leaving while refusing to compromise or respect her wishes.
I can see where you're going with this using personifications of positive and negative emotions, but there's nothing in this story that actually makes me want Hope to succeed more than Despair. It seems Soul is only being torn apart by the conflicts between the two, not necessarily by the presence of Despair, which implies Soul would be just as well off if Despair remained and Hope left.
This little conundrum, also: was Sadness happy to see Despair?
The frame of reference is weak, as the only way we know is that Drew is sixteen. That and economics means the school is probably a high school. I can only assume this takes place in present day.
You only mentioned Jane's last name once, in the first scene where you introduced her. If only important enough to mention once, you probably don't have to mention it (or even bring it up) until her last name becomes necessary information.
The style and structure isn't bad. The sentences flow smoothly and there are very few grammar mistakes. However, I fail to see the need for chapters. I copied the text into a separate document, removed the chapter headings, and it read exactly the same. Perhaps use chapters for different days or for major locations. (Home, work, whatever.) There is also information that could be relayed differently. For example, with Jane's diary, don't tell me it's the kind you can pick up at the dollar store, show me that Jane had already picked it up at the dollar store. Otherwise, it's you as the author intruding into the story to deliver information which should be done so through the character's interactions.
The first paragraph is very jarring compared to the rest of the story. It's difficult to tell if this is you as the storyteller directly addressing me as the reader, if this is something Jane is currently contemplating, or if this is a short prologue. However, the shift from this to Jane is very abrupt. This could be remedied easily by inserting a blank line between that and Jane's introduction.
It seems you have a good thing going here, but it's not going anywhere. It's just a vignette of Jane trying to stay awake through the first day of school. There needs to be some sort of conflict, a problem she needs to resolve.
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