Allow me to be critical about this critique here.
This does contain a good deal of spoilers about the next chapter or two, so be warned.
The whole plot line right now is rather fast and I understand that, but it was my intention to quickly paint a rough picture of what Asterian is like when faced with intense situations, what's going on in his life, and so on before toning it down a notch and slowing the pace. What I'm doing - or at least striving to emulate - is somewhat similar to what MLP:FiM did during the first episode: It told a story that spanned over 1000 years as well as some of the personal life of a pony and condensed it into about 10 minutes. Also, my idea was to slam Asterian with these problems because even though the odds of all this happening within a day are a little ridiculous, I thought it would be more prudent to condense the first couple of hardships into a chapter or two, then slow the pace to one that makes a bit of sense. It somewhat relates to the way negative things are perceived to happen in real life - everything bad seems to blur together into one day, only this time is actually
happens in a day. I'll explain further on this within the story.
Miss Pine would have sent Octavia to Asterian because she knows he was in charge of inventory and is a writer himself, so she could logically assume he had a small cache of ink and other supplies. Miss Pine's supplies were actually repossessed along with the shop, and the ones that she's smuggling out of the shop are essentially stolen.
Octavia has just always been a name I liked, but I just thought I'd introduce a small joke into the story by her saying that. Asterian's attraction to her is nothing more than a physical infatuation at the moment, but I'll likely change that up.
This actually is the first time Asterian has heard about his debt, but this will also be explained later as the mortgage company had confused his payment records with another pony's - things had been in disarray at the company since it was reformed. On the subject of money, Asterian is a usually generous pony, even if that means a small self-sacrifice. His infatuation with Octavia also influenced his decision.
As for the last bit... I can't really defend that well, but he does know that losing his home and job would also mean leaving everything he holds dear behind him. He was born and raised in Ponyville, and he would probably never see Merriweather again if he couldn't take care of himself. He does have friends, but the stress of the moment was simply overwhelming and it clouded his judgement, and as we know from his trip into Everfree during Darkness - Part I
that he is regretting his actions. I don't think anything
merits you to wish your own death, but Asterian tends to lose contact with positive emotions if he becomes stressed, even becoming somewhat lifeless - which I may need to add to the OC page.
You definitely raise some good points, and having carefully considered everything here I might be able to answer some questions (and raise new ones) within the next chapter. Thank you!