You reference taking out a HELOC and those are generally provided when the property is in your personal name, which I don't recommend for investment properties.Overall, it sounds as if you're tired of dealing with "long distance" ownership.

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.  

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

Despite the fact that the market has dropped significantly both in rent and price, I still think the market should be considered high risk/high reward.

Happy to help --What are you referring to when you say you specialize in this specific issue?  

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. 

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