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The advice is to overwrite and I'd agree with this. I used to struggle with this aspect of writing when I first began story writing. Maybe that's why I rather like flash. It's short and to the point. No time for backstory. You are straight in on the action.
Overwriting allows for the very important aspect - editing. And friends, editing also means cutting. It is far easier to cut than add. If you are submitting a piece of work which has a word limit, then you must stick to that. I can always remember when I was writing essays for an OU course how people would complain that they had 'so much to say that it wasn't possible to get it in to the word count.' Oh, yes it is! Word limits there for a reason and are great for honing your editing skills. I've cut hundreds of words to get a piece to the right word count to submit. It's amazing what you can cut without losing the story.
Adding to a story can end up being filler. Trying to plump out a manuscript. It is much harder and may well reflect in the work you have put in. I had this problem recently, and totally my own fault. I misread the word count and had a novella ready and waiting to go after an edit. I sent it my proofreading friend and then thought I'd just check the submissions process again. Horror! I was six thousand, five hundred words short of the minimum requirement. At that point I was ready to give up. That's far too much of a gap to fill. And then I thought, could I do this?
I emailed my friend and told her to hang fire reading it because I was going to try and rectify the problem. I felt I had an original story, and I loved it. What I will say now is I can't stand reading it again and can't see the woods for the trees. I got there, adding three new scenes and inserting new work into my original scenes, but does it work now? I can no longer be the judge of that. I have asked my friend to be honest and let me know. She's the kind of friend who will. I can only wait and see what she says. I'm pretty sure it's littered with mistakes. The first thing she said when she printed it off was that I had two chapter 23's. That didn't surprise me.
So, my advice to you is to overwrite and then cut. It's a nightmare doing it the other way around, unless you are only short by small margin. I am proof of that.
I will let you know what my friend says about my manuscript. I'm expecting the worst! The good thing is that I kept the original before I doctored it. I wouldn't want to do that again.

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