I’m active duty Air Force with four properties.

So the rent is paid, but he is disturbing the neighbors, or stealing things, or smoking cigarettes indoors or something.

The restaurant will have a 1500 ft2 patio as well as the 3500 ft2 indoor space to finish out the design.  

I’m still up in the air on this.  

I am eyeballing my first Air B & B in Fox Lake, or neighboring town, on the Chain O'Lakes.

Will you rent through Air BnB?

There will be some holes in the wall where they open it up to let air in and dry it out.

It's the visual thing for some people mostly, with such small wall space having it right there in your face isn't ideal. when at all possible, every flip will just get duct work and standard air conditioning. 

Are you going to pay your rent, or skip rent and book an Air B&B? 

But all well maintained with central heat and air.  5 of the 7 were vacant.