Look into Illinois first-time buyer programs for potential grants, and think about leveraging business credit once you’re established.Good luck!

I know pools are a must have amenity to compete in many markets and I have to admit that I'm a bit hesitant to enter those markets due to the potential liability risk.

For southern states, you might want to look at smaller markets in Alabama, Mississippi, or parts of Tennessee and Arkansas where properties are still affordable and cash flow potential exists.

Known  Potential Black Swan events, numerous.  

Although I saved 20-30k by doing everything myself and learned a ton in the process, doing that sucked up all my time and potentially stopped me from buying multiple multis last year.

You can still find solid investment properties at reasonable prices, which can lead to strong cash flow.Diverse neighborhoods: Cleveland has a wide variety of neighborhoods, each with its own character and investment potential.

I've never heard money/profit described as cute, so it's not important.The most important thing you mentioned, was the rent potential and ARV. 

This is how I see it:Single-Family Homes:Pros:Larger pool of potential tenants (families).Simpler management (one tenant, one lease).Often easier to finance.May appreciate faster in some markets.Cons:Only one income stream.Vacancy hits harder financially.Duplexes:Pros:Two potential income streams.Live in one unit and rent the other (house hacking!)

I want to be able to find potential markets/listings nationally based on the return.

I’m currently targeting properties in the $200K–$500K range, depending on the location and potential cash flow.