The bad news is that your idea has a few major flaws besides the fact that you absolutely must disclosure your intent to any landlord according to the 2020 IL TLRO Tenant Landlord Residential Lease Ordinance - the most obvious of which is that you are leaving yourself as an individual open to enormous personal liability.

This will be the first time moving beyond an individual condo investment. 

Its not on MLS, its from a private individual. 

But you clearly didn’t do your Due diligence when you did the background check on the individual that you went to your house up to.

I am a former social worker and have sympathy for this individual but this is my business.

Hi Damon, If you are a self employed individual generating earned income and no employees the solo 401k would be a great tool to consider.

What is the best way to find and introduce myself to these individuals/companies

looking to connect with like minded individuals and meet other investors, please reach out if you're interested!

We absolutely dread our day jobs and looking into making investing a full time endeavor.

Individual circumstances are highly variable and must be taken into account when tax planning.