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.

Would banks typically provide a HELOC on an investment property, and if so, what terms should I expect?

have you considered bringing in an equity partner to provide a loan?

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.

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. 

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.

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

@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. 

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