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.

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

A key risk is the due-on-sale clause, allowing the lender to demand full repayment, though enforcement varies.Keeping the property in an LLC provides liability protection, shielding personal assets from lawsuits.

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. 

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

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...

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.