RE: STEEM 2020; What I am going to do!
Completely agree about the hurdles of bringing new people to steem - out of five, one has got as far as posting, it feels very complicated to him already and I've only told him half the story. We've not touched on tribes, claiming rewards, powering up ... the list goes on. Actually getting him an account was a job and a half, eventually I set up one of my claimed accounts. I would guess so far getting one person on to Steem has taken about fifteen hours of my time, never mind his, and I'm not sure he is even going to post again.
Your idea about mentoring is brilliant, and so needed. I think it's needed at every level, whether people want to write long form posts or engage people with shorter posts.
I talk about Steem now in terms of owning part of the platform rather than earning. Even if Steem was greater in price, I don't feel that's a helpful idea because withdrawing that value from Steem is implicit. Being able to buy Steem directly from fiat would be marvellous!
Good luck with your entry and pursuing these ideas at SteemFest.