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Date: 2011-07-18 03:57 pm (UTC)I've entered quite a few that I haven't one, and one that I placed (there weren't winners or losers, just people who placed). It works a lot like sending things in for publication. You send something in, and see if it works. I tend to use the same qualifications for sending stuff in as I would for publication. (i.e. what are they looking for? And then I send in the best piece that I have that is written for their specs.) I would avoid submitting more than one, unless they're fairly different stories and you're not sure whether they'd go for more of a cute or melodramatic story or whatever...otherwise, I think it can appear like you're "spamming" them.
I do avoid all contests that involve paying entry fees - that always strikes me as fairly stupid. But I'd totally enter it. What's the worst that can happen?