Of course I submit to the same publication over and over. How else can you reasonably expect to break in? Editors not only don't mind, they EXPECT it.
As an editor, I don't care how much crap a writer submits, or for how many years he submit it. It takes time for many to learn, and that writer who has been submitting crap for years is not a problem. Now and then something clicks with such a writer, and just like that everything he submits is good. I've seen it happen many times.
As an editor, the only thing that bothers me is when everything a writer submits is simply not appropriate. It may be bad, it may be good, but it simply is not appropriate. It doesn't fit in any way.
This tells me the writer isn't reading the magazine at all. He's just reading the guidelines and firing stuff off. Some few writers can pull this off, but they're usually experienced writers, and at least look at the index, and do enough research to learn what does and doesn't fit.
Which does not mean I don't want to see things I haven't done before. All editors wants to see things they haven't done before, but they still have to come in context, they still have to be something the particular readers of the magazine will enjoy.
Anyway, you don't have to tell me you read the magazine. The stories you submit will tell me this in a much more honest way.
Perhaps the most famous case of a writer submitting over and over to the same magazine is that of William Saroyan. He write to the editor at Story, saying he was going to submit a new short story each day for a month. He did so, and along about day twenty or so, the story he submitted was The Daring Young Man on the Flying Trapeze.
The one story made his career, and he sold it because he kept submitting until the editor said yes.
Now, as a writer, I wouldn't submit that often, but I usually write stories aimed at particular magazines, and my own personal rule when a new writer was two stories in the slush at the same time, one near the top, and one near the bottom. So if a magazine reported in six weeks, I'd submit a story every four or five weeks.
I'm not going to disagree with Lorna too strongly, but I am not going to buy a story because I know a writer, because I'm friendly with a writer, or because I have some sort of relationship with a writer. Nor am I going to reject a story because I don't know the writer, or because the writer submits too often, or because everything he's submitted in the past was crap. I'm not even going to reject a story if I do know the writer, and dislike him intensely.
I buy a story because it make me go wow, and I believe it will make my readers go wow. I reject a story because it doesn't make me go wow, and I believe my readers will have the same reaction. That's it. Period. Over and out.
One last thing. The writer I'm usually pretty will fail all the way around isn't the writer who keeps submitting crap, or the writer who submits a little too often, it's the writer who doesn't submit nearly often enough, or who stops submitting completely after one or two tries. Or even after ten or fifteen tries. When you stop trying, you fail.