With all my respect, most real estate agents have no clue what the laws are.

Without proper boots on the ground, your property will never get the proper love & respect it truly deserves (I get it.

From what I hear, Vrbo is much worse than Airbnb in this respect.

For example, I think when people look at rental rates in Spain they consider regular annual rentals and Airbnb-style rentals which are two ends of a spectrum and have their respective drawbacks (changing legislation, etc).

There is almost no understanding CPM- several multimillion dollar coliving start-ups have FAILED b/c they saw the demand for coliving w/out seeing the need for a respective form of property management (see HubHaus, Common, Starling, etc). 

It should be common sense that if you respect your tenants, understand the culture and provide a positive and enjoyable experiences, in many cases that is reciprocated.

It is your choice to believe it or not and I respect your decision.Just for you, these are the very first properties you see when you search Chicago.

So far a little over a year later we are a super host and premier host on Airbnb and VRBO respectively.

I respect him and what he did for BP, but that sounds like bad advice. 

Architecture did a design and well respected contractor estimated the buildout of 4 plex would be an additional ~800k for total project cost of ~1M. it would be ~1.2M for the 7 plex.