I'm still not sure how popular a Tor contest would be. Ultimately, it would require much more than just Tor awareness to be private on the web.
Tor is abused too much to be easy to use: Bitcointalk will charge you an evil fee, almost every site will either give you many captchas, or plain out block you. Creating an email address is possible, but only with providers who's email gets rejected by other providers. Even email providers who claim to support privacy won't just let you create an account, unless you'
rre willing to verify it using your phone or another email address. Privacy is cumbersome.