Good stuff! And yes it is quite long, but hopefully well worth the read and can result in many spin-off conversations on how to improve Steem at many levels.
I'll get back to you in more detail on how we will do these competitions. I have a few neat solutions.
Also while on this topic, I think it is worth bringing up the value of comments and engagement on Steem. If I write a comment to someone on Steem, it brings their attention back there to read it, which helps Steemit make money. It also makes it more likely they'll then go curate some people or engage with some content as a result of me bringing their attention back to a Steem front-end with my comment, which then again feeds that same loop. So another idea would be to encourage more of the conversations we have on slacks, discords, and elsewhere to take place on Steem if possible. And to do our best to encourage and incentivise good engagement.
Actually yes you and I both are on the same page regarding on-chain chats that we have in slack. Remember I even created the https://neosteem.com forum with all sorts of developer, marketing, witness and governance categories. Forums are also nice for quicker discussion threads, but no-one in slack wanted to embrace it, pretty much a solid day of structuring wasted. I think most people in Slack feel comfortable in there.