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.  

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

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. 

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.

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

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

If you’re working with an experienced agent, they can provide some referrals to help get you started.2.

The sale of our home will provide us with approximately $150,000 to allocate toward investments.At this stage, we feel most comfortable focusing on long-term rentals.

Cab anyone provide details