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.

She is paying the rent in full each month, but she says due to covid she can't pay the utility bill and she is trying to apply for assistance with her utility bills for covid relief.

I would suck it up and start fielding and interviewing for a new quality PM who will do their job, do it well, and than you can focus on being the investor not PM's assistant.