What you want to create are communities that will eventually sustain themselves. So you will need to work with Chicago Public Schools, Chicago Police/Fire Departments, Illinois Department of Human Services. More importantly some of the people who work under those auspices need to be a part of the community they serve, so they will feel more invested in a beneficial outcome.
There are ways to entice government workers to be a part of the communities that they serve and so we should look into doing that, and the same can be said of healthcare.
For the impoverished people in the units, you will have to find a way to engage them in their own community as well. Perhaps cooperative industries in and near the community would be a way to go as well. Having those who live in the units, certified to make repairs (which would mean educating them in trades like carpentry, electrical workers...) would help them transition off of the subsidies, but not out of the communities themselves.
But it would be nice to integrate aspects of government subsidies first, using a "Whole Life" (Not all your life" approach to the communities, that would wean people off the subsidies, but have them stay in the communities. And this could be done in existing communities that have been devastated by poverty.