They use an outside agency.

Assuming Illinois doesn't have state-specific forms that are different, look at paragraph 6 of the deed of trust that any owner occupant who got any 30YF Agency loan signed at any closing table within the last 5 years. 

There are quite a bit of 3rd party sites and agencies that will list your property for short term for a percentage/referral fee which will be helpful as you get started. 

Also be sure to look at what other requirements there are as sometimes the values need to include W/S/G depending on what agency you are working with.Best of luck

I sold my insurance agency and cashed out to go all-in on this area and I actually live about 30 miles to the east in Louisiana.  

Correct, the agencies offer financing solutions for large multi-family. 

I have been around the business of real estate my whole life (mother owns and runs a title agency) but never actually put any of my own effort into it.

The GAO is not a court....It is a federal administrative agency.

Is it even legal for an insurance agency to ask if you rent to section 8 tenants?

Can I request credit agencies to remove it from my report if I do so?