Maybe you could do something like indie hackers [1] and highlight the stories of people that are trying to get off the streets by doing online gig work. That would be inspiring for people looking for help and interesting to everyone else.
I did spend some time looking over Indie Hackers yesterday. I am unclear whether anything I do at all fits there. But thank you for suggesting it. I am trying to figure out how to get taken more seriously, in spite of it being an uphill battle for various reasons.
Nutshell version:
1. Flexible online means to earn money.
2. Genuinely affordable market based housing, such as SROs.
I have several blogs where I talk about such things, like Mic Digs, Project: SRO and Write Pay. They don't get much attention.
Edit: just to prove my point, here is a recent piece on working for pay while homeless. I have submitted it to HN. You can go watch it be ignored:
https://news.ycombinator.com/item?id=15682882