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. 

Best of luck, but again, I suggest hiring a professional. 

An existing duplex provides immediate rental income and proven market comparables, reducing risk.

And of course I am very good at what I do providing the money to make this happen for them the key though is there is no debt I provide cash we own it outright and I  have a JV with my clients that do the work of finding these and dispostioning them and dispo is done simply on the MLS very simple. 

Contact the utility provider and get a historical average based on the last year of use.

When I asked why this was caught earlier, she responded, "Based on the timelines you provided, we had a team fail including me...

Similarly, if you are you a medical professional with strong connections at the local hospital, then target properties (and their owners) that would attract medical travelers.

If the cash-out refinance option isn’t providing enough liquidity, you could also consider a hard money loan, though these tend to come with higher interest rates and shorter terms.