But I would check to make sure she personally has employment that covers the 3x's income/ rent, is she going to be relying on child support or spousal support that may or not get paid to make the rent?

I wouldn't rely on the tool you reference above.

I would not rely on being told something was "new".    

Of course, I do not solely rely on the tenant and am not shy about a thorough inspection. 

Could potentially rely on liquidating distribution to avoid the withholding taxes on dividend.  

By this, I mean that you need to rely on yourself for training, etc.

I do not feel comfortable in relying solely on Social Security as well as my 401k/Roth IRA/Investments to get me by.

While requirements vary by program, many state the requirement to be not owning a home as your principal residence for 3 years.  

(Near Chicago) but do inspection prices vary by state, size of house, or just the inspector?

Look for a down payment assistance program to cover the majority of the 3.5% down payment (varies based on your state).