That’s a tricky question, Paul. First off, you have to realize that all screenplay contests are *money-making operations*. They don’t do them as charity. I really don’t like the way they tease out “here are our quarter-finalists,” then a few weeks later, “here are our semi-finalists,” and so forth. And they all seem to do it, even the Nicholl. By making a certain level, it provides — in theory at least — some objective measure of a writer’s progress. Practically speaking what it entices the writer to do is enter the contest again.
However, I’ve known writers who were motivated by their script’s placement to keep writing and over time, they got represented. I never say ‘never’ (although I just did), so while I’m tempted to say “Never enter a screenplay contest,” if you’ve got the discretionary income and you’ve done your homework on a particular screenwriting competition, it’s your choice. The only two that have much credibility as far as the industry goes is the Nicholl by a long margin over anything else, then the Austin Film Festival contest.
Bottom line, the REAL contest you’re trying to win is to get an actual buyer, producer, or rep to say, “I like this script, this writer has got talent and a voice.” To do that, write a great script. And to do *that*, focus on the writing.