While I like this idea, I barely have time to manage this contest, that's why I'm looking to automate as much as possible. I guess we could apply some sort of semantical algorithms on these posts, but I don't know how reliable it would be. :) I am also opened for joining forces with someone who is willing to oversee this contest, and be a judge for these "essays".

My biggest concern, with this idea, though is that I'd like this contest to be as simple as possible for the participants. The goal is to give people, who are new to both projects, a chance to feel more involved without having to spend hours on writing contest (and potentially not winning). Saying that, they still have an opportunity to resteem this contest and promote both projects.

Perhaps, I could include more engaging contest on both projects, so when people share it, it would be more informative to new users that are not familiar with these projects.