So I'm gearing up to write an actual full-length novel and I've decided that the best way to test the mettle of my writing (and make a couple of bucks in the process) is to enter a few writing contests.
But I simply don't have the time to write a brand new short story for every. single. contest. Plus, I'm a bit lazy. And I would really not like to waste six months to a year ignoring my wife and children just to write a book that will never break into the top 100,000 self-published Kindle books.
So I think that entering a couple dozen contests in the next few months is a good way to see if my friends, family members and former instructors have been too kind in their praises. I figure if I can't win a contest or 12 then I probably shouldn't waste my time on a novel.
Presuming my logic is sound on having my writing judged via contests, many, if not most, writing contests that give out cash prizes explicitly state that they do not want submissions that have been previously published -- a thoroughly understandable condition.
So here is my question: If I only have the time and/or desire to write one or two short stories of quality, is it ethical or proper to submit the exact same unpublished short story to multiple contests?
Feel free to explore other tangents if they relate to your answer: If I was fortunate to win two different contests with the same story and I got found out is it likely I would have to forfeit one or both prizes? Are contests not a constructive way to gauge the grade of your skill? If not, what is an excellent way to have your work peer reviewed (preferably for free by a professional)?
You certainly don't have to answer these questions; I have no problem saving them for another day for the Writers SE.