I'm definitely on board with you and will have to think on it some more. I saw your first post after I had initially made my comment, so that definitely helped to frame what you had in mind a little better.

I think your first challenge is a great one! Not only does it allow users to bear their soul (which is pretty necessary for an 'overcome' story) but also ideally helps others to get a better idea of who that writer is as a person. It's frequently forgotten that we all have our current imprints/reactions built from personal history and experience.

Some similar things I've seen around here that may be useful include Random Acts of Kindness which focused on the 'here and now' of paying something forward (commonly SD's) and Hearing about previous kind acts that focused more on past experiences of niceness.

I do think that stepping outside of the post/writing experience itself is necessary here. Every single person here checks their post payout form the previous night, with the hopes of seeing it 'pop.' And I'm not saying this is wrong, but it's an impediment in my mind when the focus isn't just on individual positivity but for the whole community itself. Especially considering how anything over a week or two old here tends to get buried and forgotten about.

So, my outside the box thoughts....
Generate a discussion on a community mission statement. I understand the want to get away from 'facebookers talking about facebook,' however this place is rather distinct from other social networks in that, simply by having the economic backbone that Steemit sits on, longterm and impactful solutions become readily available. No one on FB has input on what FB does, how it generates money, or where that profit is spent. Users are completely disconnected from those who run the site and commonly vice versa. That's not the case here.

With this in mind, a discussion between smaller/newer users with those at the top (whales/witnesses) is a HUGE must in my mind. Just having @picokernal (and recently @ned for a Q and A session) come into steemspeak to give those in there a better idea of what's going on, intentions, things in the pipeline, etc.. was insanely helpful to me personally, so that I could convey that to users both in and outside of Steemprentice. I'm by no means saying that general users need to know and understand everything, but things like this go a LOOONG way to being able to give those founders/whales/witnesses the benefit of the doubt on their intentions. Even though it's rarely discussed, often success is both a combination of writing (or other) skills AND how much somebody likes/trusts you as a person. On steemit what we are really doing is branding ourselves with our posts and behavior and ideally fostering people to come together with enlightened self-interest.

While this can be done in a post, using other methods like a chatroom and/or voip can do a lot. Since having a large number of people try to discuss things at once can be a problem. What I propose if generating about 5-10 issues that are inhibiting trust (on or off this site), allow people to join these 'sub-groups' to come up with a proposal, which then at all brought together in a larger discussion or post. Much like politicians (i hate to even use that word here) do with work in a sub-committee before taken to the whole community for discussion. The big difference in this case is that people can freely join whatever topics they are passionate about. It's the discussions that are really needed.

Long story short, i think both sides are needed...focus on personal positivity AND community trust and positivity. Otherwise we just end up with a bunch of happy people (which is great) that don't also have the community, of which we are a part of, in mind too.

Anyhoo, i've already got a wall of text so i'll end this here. But i'm sure I can think on this some more.