. - I am a General Contractor, too, here in Chicago!

Well they are likely going to tie up the property with a lease, contract or both. 

There are a lot of community redevelopment block grants available as well as tax abatement programs to take advantage of.

The goal of a large number of real estate investors is to have a large enough real estate portfolio generating a large enough amount of cash income to retire from whatever their “8 - 5” is, be that corporate employee, independent contractor, or business owner.  

I was browsing NHS' website and ran across their "NHS Redevelopment Corporation Liens Available" page. 

So, I tried to help the situation by getting a contractor to go replace the floor and remodel the bathroom so that the house is nicer for her.

You'll also want to prepare a personal financial statement for each of the guarantors/owners of the entity, the entity documentation, 2-3 months worth of bank and brokerage statements for each guarantor and the entity itself, any plans, specs, etc for the property, information on your GC, and a detailed Scope of Work from your contractor along with the draw schedules they expect.

Contractors win.

You can try to outsource that experience to general contractors, property managers, agents, and others (I highly suggest you do), but all of those services will eat into the last "R" of repeat. 

Should I begin by looking for a contractor?