I agree that contests are not a route you should choose as a way of breaking in.
Only the creme de la creme, i.e. Nicholl have any real standing or prestige. That's primarily because enough agents and prod cos have read enough winners of the non top tier contests to know that the best of the batch of submitted amateurs, does not mean the script is of a professional caliber.
For that reason, I suggest that when entering contest do not expect anything beyond the tangible prizes - i.e. cash, gifts, software, feedback, etc. If a contest prize includes submissions to specific agents/producers/managers who have agreed to read the winning scripts and/or meet with the writers, that's one thing, but for contests that make vague promises of "access" or publicity, be aware that aside from stroking your ego by seeing your name in a press release or ad in Variety - nothing more will come of that publicity or access.
While feedback/coverage/notes by a professional consultant as part of a prize package can be a valuable prize, I'm in agreement that contests that offer feedback to all entrants (or offer the option of feedback for an additional fee) is not the plus it appears to be. As has been pointed out, many of these contests use amateurs who have no experience in development, especially in the early rounds when there's a high volume (hundreds or thousands) of scripts that must be read.
Very few established readers or screenwriters are going to read scripts for ten bucks a pop (or in some cases for nothing) and most screenwriting contests can't afford to pay more than that. So they have no choice but to use newbies to read the first few rounds. In the late rounds of judging, when there are fewer scripts to read and winners are picked, the big guns often do the reading, but the notes are usually written by the readers in the earlier rounds. But what's the value of getting feedback from someone who may know less about screenwriting than you do? Unless there's a guarantee that the notes or coverage is provided by industry pros, don't waste your money on getting feedback.
There are some contests that offer prizes that can make it worth your while to enter. The Screenwriting Expo contest usually has a pretty large cash component to their prize (I think last year's was 20K).
Ken Rotcop and Devorah Cutler-Rubenstein offer a hybrid workshop/contest a couple times a year through the Writers Store. A two day class on the first ten pages, then participants submit their first ten pages - the writer with the best ten pages wins agency representation for a year. The class itself is worth the price of admission (I think it's $100 or maybe $200).
But overall, contests are a waste of money - you'd be far better off taking a class. or getting an in-depth evaluation by a pro, or subscribing to the Hollywood Creative Directory and querying producers and agents you feel would be a good fit for you and your script. All far better uses for the money you've budgeted for pursuing a screenwriting career.
