I just read your "Our Plan for Onboarding the Masses" post. I gave critical feedback, but it might get lost in the long thread trail so I am posting it here. I believe the fate of Steemit will be determined by what you, the Steemit Development Team, will accomplish in the next quarter, possibly two quarters. You wanted feedback, here is my assessment and recommendations!

If you are looking to strike a chord like you did when Steemit came out, you are missing the point. Back then Steemit was unique, for the reasons you mentioned. But now, there is COMPETITION! You must be better, faster, easier, and more in tune with the audience you want to attract.

So, here are the short points to success. I will keep it brief, if something doesn't make sense, then ask why.

Kill the bots. No more auto-voting or auto anything! This is a social site people!!! The very strength is having people contribute, either by posting content, curating, or simply adding to the conversations. So KILL the bots. They are caustic, drive people away, and make it so even the invested don't have to participate.
Reward the authors of good content. Upvoters/curators should also get a reward, but much less. Without good content, Steemit fills up with crap posts that only the bots care about.
Make posting EASY. Enough of this markup language crap. Every other site I use makes it easy for content to be posted. Steemit is one of the MOST DIFFICULT to post anything. I rarely use it anymore because of this. Allow for short posts, links to external articles with user commentary, and a simple interface that does not require HTML knowledge. Go out to Twitter, Medium, LinkedIn, Uptrennd, Minds, etc. to see much better interfaces.
Market across traditional venues and with word of mouth, when the reputation improves. Here is the thing, yes it is painful to say, but many (perhaps most?) of the good writers have left. Bots rule and the whales grab most of the rewards. So what do you expect word-of-mouth marketing to promote? Right now, nothing. So, if you are going to get people to try Steemit, it will be with more traditional marketing maneuvers.
Don't waste time on 'Communities'. It is premature to focus on 'Communities', as most of the activity are by bots anyways! First get competitive, then lure people in with a great experience, and once you have real content, real interaction, and real excitement, then worry about things like 'Communities'. If you spend you energy on them now, you will end up with a bunch of dead/nearly-dead communities that are only being used as another tool by bots. This will distract you from the real opportunities you must go after.

We need to fix issues, be competitive, and reach out to the vast social media audience who want a functional 'Steemit' experience (in that order). If Steemit does not deliver, they will go to Uptrennd, Minds, Hyperspace, Publish0x, BitTubers, or a list of other contenders. I already see a lot of Steemians on these sites who are more active there than they are on Steemit. That SAYS SOMETHING! (and it is not because Steemit is missing 'Communities'). Fix the reward system, remove the auto-bots for real social-interaction, make it easy to post, and then use real marketing practices to showcase the improved Steemit.

Otherwise, I doubt any of us will be here next year.