The twitter posting above from the great Jazz Guitarist Russell Malone summarizes pretty much how I have always felt about competitions. For me, it's like going to Las Vegas and gambling. I know I'm going to loose. What's the point?
Now that I'm older and not eligible to enter the Competition (see the rules here), I have a little different perspective and I would give different advice to myself. Even if you're not going to win, if you had a point you were trying to make, your reason for going through all the trouble would be to make the point. Looking through a lot of the submissions (actually the only person I know who listened to all the submissions was George Klabin, president and founder of Resonance Records--I wasn't even in the top ten with 72 views), my impression is that none of the guitarists actually used Wes Montgomery's three-tier approach to improvisation (single note, octaves and chords) or many other aspects of Montgomery's playing (see my discussion of Wes Montgomery's approach here).
One strategy you might adopt as a contestant would be to actually apply Wes Montgomery's approach to your submission. For me, at least, the main purpose of the competition should be to keep Wes Montgomery's music and vision alive. Unfortunately, the stated purpose of the competition was to "find the generation's next great jazz guitarist," which I think is a mistake. No competition will discover this person for the jazz audience. A submission that really kept Montgomery's vision alive (and maybe even extended it a little, if that's possible) would at least have to make the judges pause for a moment.
Maybe great facility and fast playing always win competitions but those were never Montgomery's goals. And, maybe Wes would have never won a competition or even bothered submitting (he had to be pushed to originally audition for Lionel Hampton). He was far too modest and self-effacing. I think that is Russell Malone's point and I completely agree. But, there is still a part of me that likes to make a point, particularly through my playing.
In future posts I'll try to lay the ground work for keeping Montgomery's vision alive.