Forking it over for fame

Since I finally received the last rejection letters I was waiting for, it's now time to reevaluate my writing, maybe spot edit a couple of works, and send my babies back out into the cruel world of publishing. This time I was thinking about entering my works in some contests. While there is less of a chance to actually get published, the stakes are higher when it comes to the rewards. But there is the little catch of having to pay an entry fee.

I see the need for entry fees, especially if the contest is rewarding the winners with a nice chunk of change. But how do you evaluate your work to know whether it is worth it to pay out $10-$20 for a chance at getting published? From my own experience, I know that my perception isn't always focused on the quality of the story, but my attachment to it. I have paid up to $20 for a contest entry before. Once the contest was over and I didn't win, I submitted the work to another magazine. Lucky me, I sent it in to a magazine that provided a little bit of feedback. Turns out, there were a couple of fatal flaws in the story that I should have picked up before I sent it anywhere. That proved to me I wasted $20.

If you were to submit a poem or a short story to a contest, how would you evaluate your work to see if the risk is worth the reward? I know I still have to come up with a set of standards before I think about dropping any more money on contest entries.