One of my students is playing in a banjo contest this evening. First prize is $200, so he's really hoping to win. This is not the first contest he's played in, and I think he'll do pretty well. Yesterday at his lesson we worked on his contest numbers: "Big Tilda" and, if he needs a second one, "Whitewater." We were working on "Flint Hill Special," but the contest rules said no tunes that use Scruggs tuners, so that one had to go.
I'm not a big fan of contests. I played in two of them when I was younger. At the first one I took second place, which I was satisfied with. At the second one I didn't place and, in my humble opinion, the people who won were not better players than I was at the time. That was my last contest.
One reason I don't like contests is that the judging is so often biased. The local favorite often wins, and the judges often know some of the contestants. The only really fair way to run a contest is with blind judging---that is, when the judges can't see the contestants and the players have numbers rather than using their names for identification. That's the way the prestigious Winfied Kansas contests are run (I judged the banjo category one year) and I believe that to be the best way.
But my student is, to some degree, part of a group of kids who see each other at different contests, and his band is playing in the band contest at this same event. I think that's probably the way to go into contests---go to have a good time and see your friends, jam some, and if you win some money, that's an added bonus. Because music, first and foremost, is not about competing, it's about entertainment and social interaction, and if you forget that, it's not much fun at all!