This is important to consider. I have a related question for you. If you read a decent short story by an author, then you were reading a novel and it had similar characters and then you read to a point and said, wait the next chapter might resemble a short story I already read because the setup is familiar, would you get more excited to read or throw away the book.
So I'm fine with short stories that are set in the same universe of a novel, and having the same characters as the novel can work well too (as long as you don't drop any spoilers!)
But for the situation you give above...if it becomes evident that I've read this before I fear it might take me out of the reading experience and break my concentration. I'll probably start skimming fast, just to make sure that the text follows what I remember and get to a 'new bit'. I would prefer, in general, to read a whole novel 'fresh', if you know what I mean!
However if I adored the original short story, then perhaps I wouldn't mind reading it again in a different form, although that comes with it's own pitfalls. For example there is Greg Bear's
Blood Music. The short story came first and at the time I really loved it (this was 35+ years ago, so I am relying on my memory - no doubt if I re-read it I will be slightly dissappointed with it
). It ended on a rather dark beat. However he then expanded it into a novel and I couldn't wait to get hold of it and see where he took the ending....
...unfortunately he took it to a sort of 'Hollywood happy ending' that really dissippated the energy and power of the original short story. Meh!
My short story gives some inkling of the surprises in the novel and some parts of the world, but I'm not writing the novel as a twister. Rather my aim is to write so you as the reader kind of guess what's going on and you are yelling at the characters "No! No! That's a BAD decision!"
Yeah, been there and done that. Especially with
War and Peace. My flatmates thought I was a bit odd shouting at a book, telling someone not to leave with the cad....
I get the points here. I'm still thinking there is a balance. It's not that I'm copy pasting chapters, it's more that I'm taking a chapter and adding / removing things to make it standalone. This is extra effort, but at least for my first experiment, I found it helped me think more sharply about conflict and plot and character since I had fewer words with which to paint a picture.
Fair enough. I think if you take it as a writing exercise, it's a great thing to try. And if it does come up with an exceptional story perhaps my fears and thoughts would be irrelevant!
I sort of went the other way, and originally learnt to finish short stories of about 2-2.5k words (Which can be really difficult. Two thousand words sounds like a lot, but to ensure you have a good plot, characters and standalone story, it can be taxing and, of course, I failed a lot
.) However as I put long form manuscripts together I find myself writing ~2.5k chapters on average. I still don't write chapters like short stories though, just try and take some of the lessons on conciseness, brevity and clarity across.