Imo the big hurdle right now is tapping into people's motivation/passion. The generic user (again imo) has a certain learning curve to fight through that most are adverse to having to deal with. So right now I focus more on things that will get these prospective users to get through this, whether it be something they are angry about (which we saw work in the latest election), feel they are impactfully helping with or a way they directly benefit (like via a payout or lottery type reward.)
I will say that the bulk of what is currently in development (medium like editor, private messaging, busy.org, pushing steemit content to external sites with the upvote button such as beyondbitcoin.io, etc.) will help immensely on this front...so please don't take this as a knock on the site, just a fact of where we currently are.
To me our current focus is facebook, reddit, maybe youtube users which have already gotten used to a system. Having many of the shadowbans in place on these other sites makes it difficult to directly get in touch with those users in a low cost way.
I think the paid to blog aspect is somewhat of the impediment we run into, with many people being uncomfortable or viewing it as 'too good to be true' situation. Focusing on the community or anti-censorship side of where my mind has been going lately. This could also include a call for 'whats your personal value' posts or show me something culturally unique (like a lion outside a burger king.)
Now I'm just babbling, I'll think this all over and get something more concise in the next day or two. :)
Great points. There is a whole week so take your time. The intention of having the competition is just starting the process of thinking about things.