If not, then you probably need assistance with the tax side of things.

I also have been coming up with ideas of systems to put in place to assist me in my land lording business.Soooo... my questions are 1.Does this seem like a solid and achievable plan for a newbie with not a lot of capital?

The Weatherization Assistances Program (WAP) was created in 1976 (thanks Wikipedia) and they have been helping low income families weatherize.

We've reached out with: attempt to create a partial payment plan, provided info on every relevant grant or assistance program available to them, provided info on local employers who were hiring, and offered cash for keys if they moved out.

Contact a local real estate attorney to assist you with getting them out. 

Is there anyway my client who is a homeowner avoid paying a large down payment when she purchases a 3 flat here in Chicago?

PM/DM if you need some assistance.

Can anyone recommend a company that can assist in foundation or structural correction.

I'm working with the Section 8 tenant to apply for the LIEAP (Low Income Energy Assistance Program) with Montana.

If you're looking at out of state, there are many economic factors to consider (I.e. job growth, types of jobs, economic diversity, price to rent ratios, past appreciation, home court advantage, etc.)