This is only one area of real estate that should be addressed, and it typically involves premises liability/property management type claims.

However, after running the numbers accounting for insurance, PMI, taxes, vacancy, capX, property manager, etc. the property is estimated -1.85% cash on cash return (-$600/mo) once I fully rent the property.

There is a Fund of Funds involved.  

After multiple calls and emails about the matter (even involving the local HUD office), I finally get a response that says "Unfortunately, HACW is experiencing a temporary shortfall of funding and will be unable to pay the HAP amount for this month..."

In my experience, the cash flow may be substantially reduced (or even become negative taking into account interest rate of original loan and refi closing costs).

Being deeply involved in the local real estate market, I stay connected with wholesalers, realtors, and local investors who often share opportunities.

If you do take on new debt or collections during this time, the lender will see and it will require that it be accounted for in your DTI (unless this is a DSCR loan). 

I would also encourage you to get involved in networking groups in the Chicagoland area as well as listen to the straight up Chicago investor podcast.

Having "real estate investing" or "real estate" anything, in your LLC name will surely raise red flags for banks, especially as you move beyond net 30 accounts to larger credit lines.

True off market deals are ones that you find yourself, direct from the seller without a wholesaler or any other middle person involved.