My question is - at what point do you know you are good enough to send out some your short stories to publishers for consideration?
The obvious answer perhaps is to send them out and judge by the amount of rejections you get back. However (bear in mind I'm not quite sure how it all works), I don't want to send out terrible stories and have publishers groan when they see another one from me on the slush pile. Forgettable stories I could probably handle, but being the author of such horrible stories that they have preconceptions about any new stories I send in may not be such a good thing!
So, how did you know? Did you just start sending them out? Did you wait until you thought you were good enough or people that had critiqued your work thought you were good enough?
I'm not sure if you can know when you're ready. If you have some stories critique by volunteers here that would at least make them just forgettable and not horrible.
But than again most editors who have been in the business, probably only a year, will have already seen it all. And most editors will be able to tell if your story is worth reading by the time they finish the first page--13 lines-- so more than likely they won't get to the horrible part. I say most because some of the newer online editors seem to read the whole story anyway.
I've been told by a pro editor that most editors will not recall your name anyway, unless you're one of the blessed ones who can sell a story first time out, they have too many stories to read to recall every name. Even the very bad writers.
My first stories were most probably lousy, I thought I knew what it took to write a story but I eventually learned that like any skill set you have to learn how. I think you already have a head start on me back then. So in other words you're probably already know enough to be beyond horrible.
I don't if any of this helps or encourages but I say go for it. That is one way you learn.
If not, why not send it out? I have only sent out one story (I want to be a novelist and so far I have only 2 polished short stories I don't mind having my name attached to- one is at WOTF and the other is shopping around). But after hanging out on the Nano boards for a bit, I figured I would not be the worst thing being submitted. I think my name is a bit more distinct than most people's so I guess there is a chance editors will remember it, but I'm not too worried about that. I proof, have had it critted, to be bad enough to stick out amongst the hundreds of others would be pretty impressive.
If, however, you doubt your own judgment, find someone you trust. Shoot it off to a few readers here on Hatrack who would be willing to read it, and if the response is generally good, you can take it to the bank. Find a wise reader you trust to give you feedback.
For what it is worth, if you were hoping to submit something, I'd be willing to read it for you to give you my take on it.
With WotF on the other hand, I can get back a tiered result that helps me place how strong my writing has become. This helps rule out some of the randomness I might encounter when submitting and is certainly a confidence building exercise as I think just about anyone who has ever submitted to WotF will attest.
If you're not sure that WotF is for you, also try some of the full story challenges here that occasionally crop up (like the current one) as it's an even more forgiving environment and pretty much everyone else is an aspiring writer in the same boat as you.
Otherwise, don't sweat it. Have a few people read your story start to finish, point out any mistakes or tell you if they got bored or annoyed or stopped reading, fix the mistakes (including upping the interest level if it's a boring story - life's too short for boring fiction!) and then SEND IT OUT. Take this advice from me, I don't actually follow it myself.
If you're looking for feedback, you're more likely to get it from a non-paying or token paying market, unless you're REALLY confident about your story.
Choosing a market for you story is important. That's why going to Duotrope or (I can't remember the other place it begins with an R and someone else can let you know on the thread. I use Duotrope. It has a search capability that allows you to go through the many markets to identify probable market candidate.
For example, if you write hard SF, you can pick a market that caters to hard SF. If you write heroic fantasy, you can find a market that buys those kinds of stories. Submitting to the right market will help you get comfortable with the process.
If you care about your story enough to have "done your homework" and learned how to present your story in a clean, clear (no smudged ink, for example) manuscript format, that can help editors and first readers to not remember you negatively.
Please don't get obsessive about manuscript format though, okay? The story still matters more than the format.
Don't worry about any of this, just send your stuff, that's the only way it's ever going to get published. If you are remembered I think an editor would be pleased to watch your progression over time.
But, on the other hand, those stories were lousy. The editors of the day were doing me a favor rejecting them. It took about eighteen or twenty years and somewhere over a hundred stories to better myself. I wouldn't send that early stuff out now---except as a joke or something.