Great question, Alan. The irony with contests is that many times the “prize” is getting your story published in that magazine. Oddly enough, this is the same result you would likely get if you submitted that same story through the regular means. Honestly it seems a bit silly to me to pay an entry fee just to get bragging rights. Of course some contests do have prize money involved, so in those cases maybe it’s worth taking the gamble? You have to weigh the pros and cons of each contest.

Take my answer with a grain of salt, as I myself have never entered a contest. Even when my MFA program held a chapbook contest post graduation (with no entry fee, btw) I opted not to enter because I didn’t feel right pitting my work against that of other writers, particularly that of my closest colleagues. That said, I have no problem with contests for writers in general, as long as they go into them with their eyes open.

As for getting feedback, my gut feeling is you’ll get much more in-depth feedback from a good critique group or critique partner. If your goal is to get feedback on your writing and you don’t have a critique group/partner, there are other alternatives than entering a contest. I’ve found that one of the best places to find critique partners is to take a class and band together with the other students once you’ve gotten to know their work and their style. Then you can keep meeting outside of class and–guess what–it’s free!

Hope this helps!