I would say the biggest hurdles are as you described, plus 1) stunning misunderstanding of how the platform works, even by supposed crypto "experts." (Take a look at this video full of unbelievable misinformation and consider leaving a comment expressing your reaction.)

And 2) the incentive of the site for people to regularly sell at any price, because people are being supported by it. That's not going to go away, since the nature of the site is to pay people and many of us would love to be earning enough for full support from this, but that just means there also need to be incentives to not just hodl, but to buy more than goes out in related rewards.

There is a group called oracle-d that you should check out that has an incredible business model for doing exactly this. I'm going to be participating in their work. Basically they have people commission content here on Steemit (mostly crypto stuff) for upvotes, but the outgoing upvote value can't be as much as the invested STEEM is worth. So it automatically grows the STEEM holdings pool while making sure only a portion of the upvote power gets paid out.