Hell, my family came to town to visit and I bought furniture and they all stayed there before it was mine :-)

@Daisy RuizTo echo @Michael Baum, I have not seen or heard from many people operating STRs in Chicago.

The less conservative is: operate as a finder or co-GP but with very good, conservative counsel to keep everyone in the clear.I recommend you read up on "disgorgement penalties", and make sure the sponsors that are recruiting you have done the same, before jumping into this co-GP/Finder ship.

Strategic planning and phased upgrades are critical to balancing renovations with ongoing operations.

Strategic planning and phased upgrades are critical to balancing renovations with ongoing operations.

Strategic planning and phased upgrades are critical to balancing renovations with ongoing operations.

Strategic planning and phased upgrades are critical to balancing renovations with ongoing operations.

They made me move mine to $500,000, so I had a total of $2.5M coverage. 

I had a foundation guy look at mine and he suggested I put a small modine heater in my enclosed crawl space to mitigate the winter frost heaves that affect my foundation.

However to date I'm not aware of anyone operating here.