I've deliberated over this quite a bit over the last few days, but 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. For example, knowledge about VPNs, secure messaging, PGP, Linux, and general information about networking and the internet in general is necessary in order to resist the "BigBrotherNet" (a term I have made up from combining two other nouns).
I am not really confident that a single thread would be able to solve all these problems. It would require a lot of threads - a privacy board would've helped a lot with this - and they would all have to be in the same place and bumped constantly. I was thinking about placing all that information in the Bitcoin Wiki, but nobody here really reads that (or do they?). It goes on to show the challenges in informing people about these kinds of problems. I will leave this topic open so that you guys can discuss how achievable this actually is.
I'll be honest, I don't use Tor, but I'm also increasingly understanding this point and starting to think about some adjustments I'll have to make in the future.
Would a topic to encourage its use make a difference? Well, maybe it wouldn't, but it might motivate a few more to try this experience. Sometimes small things can make a difference for some.
I believe that if those who can create/provide tools that can help avoid entering into mass control, it will already be a small help.
A board dedicated to security/privacy would be useful to more easily publicize these projects and solutions.