Consider reaching out to a local Rental Owners Association to connect with experienced hosts, gain valuable insights, and access resources that can help you navigate property management more effectively.

Most hosts in Chicago just pocket the full funds from direct booking, you would be in the very very small majority if actually paid city taxes on it.

I do think that in many cases pool fences ruin the aesthetic and the Airbnb pictures so I'm sure that's why some hosts are cutting corners.

@Daniel HymanThanks for the idea but another problem I have with using the government internet is a lot of things on websites don't work because of the firewall and network settings so when I try to apply for the account it just doesn't go to anything.

Many hosts have success with a mix of RVs, tiny homes, and prefab cabins to attract different types of guests.

I find AirBNB from a host stand point much more user friendly & advanced.

Additionally, Airbnb’s policies support hosts when guests do not comply with house rules.

Did you factor in utilities, internet, etc.?

Over the years of dealing with folks on the internet, I have found most can't take hints, they need a strong dose of reality, a reality they know nothing about. 

Anything you post here or ANYWHERE on the internet is preserved almost immediately.