Yes, I think のではなかった (or んじゃなかった) means “shouldn’t have”.
Edit: here’s a link to back it up: https://japanese.stackexchange.com/questions/41452/how-to-say-regrets-i-should-not-have-x
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This is taking longer than I expected since this is my first time reading a Japanese story except for manga.
I found the first two parts easier to get through. Actually, the first part reminded me of a dream I used to see often when I was a child in a weird way. In that dream, instead of a city, I was falling asleep immediately after entering a particular store. Anyways, 
Part 1
それは
In these bolded parts, I couldn’t understand what から adds to the meaning.
Part 2
This is from the last paragraph,
もうすこしでもこうしていることができなくなったほど
I couldn’t find where or which action this bolded part refers to.
I had a harder time following the story with parts 3 and 4, so hoping to come back tomorrow after rereading them. 
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It lists reasons to explain why the town has no energy in it.
見ると、なんとなく活気がない。
No sound, everything is falling apart, not a single smoke, not a single factory…
In the second case it refers to why the town is called the Sleepy Town.
In your second question, こうしている basically means that Kei can’t go on like this not even a little further. His body is going numb and doesn’t listen to him any more.
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I promised to ask my Japanese friend about the two occurrences of おります and to get back to you all again.
In short: It’s complicated 
His first take was that in both cases it is used to show respect to the things it is attached to: On the first occasion, it’s the town (which was considered something old and therefore worthy of respect back in the day), and on the other occasion it’s the railroad (which is big and important and used by everyone, and therefore would also have triggered expressions of respect in older texts).
Then he thought about it a bit more and googled quite a bit and finally said that it might have been used in order to show respect towards the reader (the technical term is apparently へりくだる - Jisho.org). I’m having a bit of a hard time seeing that tbh, but at least I wanted to report this back to you, in the hope that it makes more sense to you.
Anyways, he thought about it and researched quite a bit and said that this is a very fine nuance that even Japanese people would not understand easily (and he’s pretty well-educated so I have some faith in this). So my takeaway is not to worry about it for the time being 
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I saw that next week will be a feast of polite and formal forms, so I’m sure there will be more complicated stuff (that we shouldn’t worry about too much) to follow. 
There were two sentences in the fourth part of this week’s story that I was having trouble with.
I think I managed to figure out the first one myself but maybe others find it useful to know. In the part with the car, there is the phrase
彼は袋の砂をつかむが早いか
I didn’t get the 早いか at first, but in the end I managed to find that ～が早いか is an N1 grammar point and means ‘as soon as ~’.
I’m still clueless with regards to my second problematic sentence, though, so any help with this one is appreciated: when Kei remembers what the old man said, the quote ends with
すると、この国の皇子にしてやる。
Wait, what?? What does this sentence mean and where did this 皇子 suddenly come from?
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There’s a couple of related phrases ～になる and ～にする, which are similar to the so called “transitive” and “intransitive” pairs. ～にする means “to convert or change something”, while ～になる is “to become”.
皇子にする would be to make someone into the crown prince. 皇子にしてやる would mean in this case that the old man is going to make the young man into the crown prince as a favor (or, in this context, as a reward). The old man is using てやる which is an informal way to say てあげる.
As to why 皇子 suddenly comes up, the old man explains in part 3 that he built this town
( he says: 「 じつは
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@Naerro Thank you, that helped a lot!
Ok, I think I finally understood the moral of the story after the second time reading parts 3 and 4. I guess reading a story from plain text takes some time to adapt coming from manga, especially when trying to figure out the context.
part 3
もう何時ごろだろう、これはしまったことをしてしまった。
This time I couldn’t solve this sentence. Again, is it referring to a previous action of ケー or is there a saying like this?
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The repeated しまった baffled me too. I think it means “I have ended up (second しまった) doing this regrettable (first しまった) thing”, the regrettable thing being that he fell asleep even though he thought he’d be able to resist..
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Glad it helped!
The first time reading this I totally missed those were the words of the old man and not of Kei so it confused me XD
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Thanks! I did not know that and that indeed helps to understand the sentence. I still think it’s just one big non sequitur, though. ”Hey, if you come back I’ll make you the crown prince of this desolate and derelict town!” 
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I guess his point was that if the sand was used efficiently, things would go back to how they were in the olden days, and the town wouldn’t be desolate and derelict any more. Or, as I’ve been suspecting all along, the old man is having fun at the boy’s expense.
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I just realized that we had separate threads for each story 
.
I will try to finish this one over the weekend before proceeding to the next one. Should be doable I think . Some of the slightly more old-fashioned sentence structures would trip me up a bit, but it wasn’t as bad as I thought it would be.
EDIT:
Alright, finished reading. It was kind of tough, I have to admit. I added quite a bit of extra items to the vocabulary list, some of which are not actual dictionary words like ぼろぐつ or 旅出 so feel free to remove these or treat them accordingly (@NicoleIsEnough chief? )
Finally, not sure if I understood the moral of the story, but:
The “sleepy town” became desolate (寂然), because it was somehow economically unsustainable or badly situated geographically, but thanks to the young one’s courageous deed (read: crippling railway industries everywhere else on the globe with his “aging sand”), to recovered and became even more prominent.
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Thanks for the honor, but I’m not the chief of the vocab sheet 
It’s a group effort (and I have not even looked at it tbh…) Please do with it what you think is helpful though! My personal opinion is that if you are wondering about a word, chances are others might wonder about it as well, and if it’s clearly not grammar, then nothing speaks against adding it to the list.
(I said “if it’s clearly not grammar” because I think that grammatical expressions often benefit from longer explanations, breakdowns, further reading links etc. which would be kinda misplaced in the vocab sheet, I think.)
But that’s just my take on it, and if others would like to treat the sheet differently, please feel free!
For the moral of this week, my take on it would be “You can’t stop progress”. The old man tried to keep society from advancing by destroying new stuff like factories, cars and railroads. But when the young man returned to the sleepy town, he had to face the fact that the sleepy town was not sleepy any more but instead brimming with modern advancements. I guess something had happened to the old man in the meantime, maybe he died or something? And despite all his previous efforts to stop new things from emerging, in the end modern society won over him.
I must say especially considering the fact that this story is about 100 years old, it feels very modern to me, with the author already pointing out the destruction and pollution of nature back then. Pretty touching, I must say.
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I think I did add the 真っ〜 grammar point, because it’s immensely useful (and because Tobira singled it out as an actual grammar point 笑) and some other misc explanations in the “Notes” column, but otherwise I agree, it would be hard to fit larger grammar points in the list.
Oh yeah, this I liked as well. I actually read the old man’s part in an old man’s voice when reading it aloud (which I usually do). It was fun .
I will cross post in the Aozora Bunko thread, since it might be useful for people. Will reference this thread as well.
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