as a glider pilot with some XC experience, and no contest experience, I can you what keeps me from contests: there is no 'on ramp'.

the only way that I know to participate in contests is to participate in contests.

What we really need is a way for people to learn about contests before actually entering one:

1. ground school -- 1 day covering eligibility, rules, launch & land procedures, strategy & tactics, traffic, equipment, etc

2. flight school -- non-competitive contests in 2-seaters

3. newbie buddies -- when you show up at a contest, team up with an experienced pilot who will be your mentor for the duration of the contest

Reno Air races has pylon school: http://airrace.org/event/racing/rookie-school/

--bob