Take a look at someone's top 100 movies. Anyone's. Do you like all those movies? Maybe. Do you rank them the same? Probably not.
Now, when you enter a screenwriting contest, you're taking a chance that the judges don't have the same taste that you do. Because, even if you write the best possible script to your taste, there's a good chance that the judges might have different taste then you.
Now, at 40 bucks for a entry fee, with thousands of possible entrants, it's like an expensive lottery ticket.
In these days of sequels and auteur writer/directors, is it even worth entering? Does a win even increase your chances of getting produced?
Many contests say good things happened to their winners(sales, agents, etc.). It's a risk, but if they're as connected as they claim to, it's worth a try..
Some contests offer feed-back on your script, so even if you don't win, you still get something useful for your money...:)
I even heard of a contest where you can keep sending your screenplay to get notes, then send it again and choose to keep getting a ton of notes, so even losing it, it's nice knowing you got your screenplay into shape...
Of course, you can skip that contest and keep using the same screenplay notes/coverage service until it's good enough for a Recommend(similar effect)...
I think it's a matter of historical record that major contest wins (and plenty of minor contest wins too) and high placements have led to representation and ultimately options, productions. Sure, the odds are long to finish high or finish a winner, but the odds are long in this game no matter what you elect to do. (Me, personally, I've had the best luck querying producers directly.)
Good questions.
Page had cred. Scriptapalooza and Big Break, too.