You are better off finding a solid property that needs light cosmetic work (paint, floors, or maybe even a kitchen or bathroom remodel), buy it at a decent discount and put 25% down or more (this is when you get best rate terms). 

Hey @Grant Woodward, you can never be too cautious when it comes to guest safety like @Lauren Kormylo said.There are dozens of things at your STR that could cause an injury or worse so making sure all the ducks are in a row and quackin' in unison is one of the most important things you can do.Like @John Underwood said, make sure you have a rock solid insurance policy that covers the pool and adjoining areas.

I have come to the realization that my calculations are not as solid at I once thought.

You’re off to a solid start, especially with all the groundwork you’ve done.

However, if your time is limited or you don’t want to deal with tenants directly, hiring a property manager can make your life much easier—just be sure to choose one with solid local experience.Are you currently house hacking in Chicago?

Denise’s approach to passive investing in larger deals would also be a way to generate solid returns without the stress of direct ownership.If you’re looking for actionable next steps:Speak with a business broker to explore your options before selling / tapping into your equity.Talk to a lender to see what financing and leverage options exist.Look into syndications or passive investment opportunities like Denise suggested.Join local and online real estate groups to connect with people successfully executing these strategies.There’s no single “right” answer, but the key is making a decision that keeps your money working for you without locking you into another job.

Cities like Cleveland offer affordable properties, strong rental demand, and solid cash flow potential.

I'd issue a notice of non renewal, do the work that's needed to get the property rent ready and find a solid tenant that will help you get to your goals. 

Based on how I am reading your summary it sounds like there is solid equity in the 2-family in order for a bank to cross-collaterize assets. 

A solid broker has established lending relationships.