Better weather and a 10min drive to the Sunset District sounds like a no brainer. 

My initial thought is a coffee shop w/ drive thru (e.g.

If the submarket (market immediately around the building/property) has high occupancy and this particular property has lower occupancy then it's likely something about the building itself that is driving the dynamic.

SFR, definitely need to drive the neighborhood.Whats wrong with Florida as a market?

I'd search for properties within a 2hr drive before looking in Florida.

When driving around town look for bandit signs and call the numbers to introduce yourself as a cash buyer. 

Common HungerIf one person has the drive to work around the clock, burns the midnight oil etc, and the other partner turns their phone off at 5pm, takes weekends off and monthly vacations, the workload will quickly become imbalanced, resentment will build, and you will need to dissolve the business.Complementary Skill SetsDon’t partner with someone just like you.

Is there anyone in the community that's open to providing guidance on how they dove into AirBnB (ideally within a three hour drive of Chicago). 

I have been consistently making calls for the last few weeks to residences I have found while driving for dollars.

Now, that you know the zoning, look for any spots greater than 2acres (“drive up” storage).