@Matt Smith - as @Christopher S. mentioned you cannot use an ADU unit in Chicago as an AirBNB as the city's intent with the program is to provide additional affordable housing. 

The struggle comes when you plan to sell, pay close attention to how the bank would treat the loan in the event you would sell.Even though its a bit more work, banks are typically open to these loans as it provides them with additional collateral in the event of default.  

These can provide good cash flow and are easier to manage than larger commercial properties, especially when you're just starting out.Also, when I was starting, I found local meetups super helpful.

My focus is on providing either turnkey-style space for those interested in temporary, infrequent use or long-term leasing for business folks who require conference room space (or perhaps event space).

On the llc side I will rent the property that I purchased from myself, and provide myself some protection of my primary residence.

Additionally, listing brokers represent what seller's provide them. 

In fact, the more issues that arise, the more profitable theses properties become for the ancillary service providers....and you want to know why these investments are pushed aggressively by so many (besides of course requiring nothing more than a pulse to buy them). 

Investors owning the one house are now feeling pinched with their own house they live in and contemplate defaulting on the mortgage.

NC usually provides better cash flow and Phoenix is characterized for stronger appreciation than NC.

An experienced investment team can provide invaluable assistance in finding, vetting, inspecting, renovating, and managing properties effectively in your chosen market.