Additionally, you might want to look into local real estate meetings.

There are even 2 gigantic "crawlspace" areas in the house that could be developed into additional ADUs.  

It's been my experience that the additional reward doesn't outweigh the additional work.

Do your management deals give you your large stake with zero or very low capital of your own in addition to a management fee?

Additionally I spent $35,000 on property taxes, $17,000 on insurance, $35,000 maintenance and repairs.  

@Madelyn Felix we used to use ShowingHero, but moved on from them to ShowMojo, due to ShowMojo offering keypads in addition to lockboxes.We've pretty much flipped to keypads as too many keys go missing from lockboxes or get locked inside the home.While ShowMojo offers a service for tenants to use their keypads after movein, we remove the keypads when a home is rented and transfer to next vacant property.PRO TIP: only use keyed deadbolts for occupied rentals! 

In addition to medical professionals, we also have college/grad students.

Assuming you don’t meet the 500 hour test, you will likely need to document the time of others spent working on your property.In addition, you need to have guests at your property as well.Until you are 100% sure you can utilize the short term rental loophole, I’d wait to do the cost segregation study.

You have consider that your average first time home buyer, has no clue how to read an LE, does not even know what fees are for what, and needs that additional assistance for them to feel comfortable purchasing their first property.

In addition, you can listen to the Straight Up Chicago Investor for great local knowledge and contacts.