Maybe it’s just gut feel, but for some reason It FEELS like these two scenarios will provide excellent opportunities moving forward, while fishing for notes to purchase at significant discounts to current principal enough to yield sufficient returns doesn’t seem as promising.  

Anyone who can provide useful advice would be appreciated.

@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. 

Try a Google search for managers or look for an investors group in the area that can provide personal recommendations.1.

What are some cities that might provide cash flow, but remain affordable?

And that is the reason why a LIRP can provide much more retirement income.You don't pay interest on the loans and the death benefit pays off the loans when you die.

Personnel Records AccessHouse Bill 3763 expands the Illinois Personnel Records Review Act, requiring employers to provide employees with access to a broader range of personnel records upon request.

Quote from @Brian Christinakis: Let's not forget the liability piece that STR insurance provides in MUCH higher liability limits for incidents ON your property but also incidents off your property while your guests are staying there (like using a bike).

Another service we provide is called an "Either/Or" - EITHER the property is Lead-Free (no positive lead-paint components) OR there are positive lead-paint components identified but still safe/habitable lead levels to reside within said unit. 

For example 1031 tax deferred exchange, BiggerPockets could teach me how to do it step by step and provide the necessary paperwork that I fill out.