The phrase Writing Contest brings to mind one word: Argh!
Let me explain.
My writing time is precious. So when a contest wants me to take time away from my novel to write a short story, it's asking a lot. Plus, I must admit, I can't write short stories. I've tried, but they always end up turning into a novel. I keep coming up with more plot twists and depth. I just can't stop at 20 pages.
When they ask for the first 20 pages instead, I'm not so disinclined, but . . .
You don't get much for your effort. I won 2nd at a local Writer's Conference, and I received 1 basket of books I never would have read (I gave all of them away), and a gift certificate for a local movie theater--even though I live 3 hours away from the location (Michelle--maybe I should mail them to you. I think you're closer).
Now, I figure I spent more money on printing and postage than I received from the contest.
This is not to say that contests are totally w/o merit. If you place, it can increase your confidence. IF the judges are competent, you will have some helpful feedback (I say if because some of the feedback I've received was downright wrong--or even marked as wrong when it was a matter or "taste." For instance, one judge corrected grammar "problems" that were correct the first time. Another docked me 20 out of 100 points because she didn't think my MS "fit" in the genre (It did. You just didn't see the paranormal aspect in the 10 pages she reviewed).
Anyway, my experience, at least with the smaller contests, has not been positive.
Hopefully, you've all had much better experiences.