A well connected agent can also tap into their network.. for instance, probate attorneys might know of people seeking short-term solutions.

You could start with your agent or a local agent who supports investors and could have contacts to refer to you.Lastly, you could consider negotiating with a local PM to take on a hybrid approach to management.  

Here's the City link for you to reference. https://www.chicago.gov/city/en/depts/doh/provdrs/homeowners...1) ADU regulations specifically exclude Short-Term Rentals so don't do it if the intention is to short-term rental. 2) The ceiling height oh 6'10" is almost guaranteed to trigger digging a basement if you want to formalize as an ADU unit, especially if that height is further reduced by pipes or HVAC. 3)Ingress/egress is an issue for renting, as is that any bedroom also will need two (ie operable window/doorway).

Save related articles to the cloud for reference. 2. 

Keep adding to your notes and refer to them from time to time.

"Big" government refers to powers, not level.

If you're still looking at this property, I noticed the reference to "LIHTC" on your report and that the property is only 9 years old.

Quote from @Stetson Oates: As a suggestion, when you refer to net cashflow, I would include maintenance, vacancy, and repairs. 

I have heard the 16% solution mentioned. 

I'm assuming you're referring to investors that provide all of the funds for your flips?