Pinellas has a lot of different cities with different regulations. 

You shouldn't do the PMs job, you are paying them, but as the first time working together I would use it as an opportunity to learn and establish the relationship.

This circumvents HR, which usually just sends me to The Work Number, one of the most useless companies since the establishment of western civilization.

You can search "[city name] short term rental regulations"Yes, you need landlord insurance that specifically covers STRs.

It's all about where regulations hit, and in MN that's at city and county levels. 

Establish a clear process for handling these requests and keep an emergency fund for unexpected repairs.Tenant Relations: Communication is key.

The requirements describe match those in the zoning regulations. 

By your logic any law regulating commerce would be valid… that’s not how it works. 

As you get further away from standard real estate practice, the risk is increased by a “legal” risk that your protection may be interpreted quite differently than you expect by a court and that the subtleties of the protection a mortgage or trust deed document provide with established law and court decisions handed down for (in the U.S.) 250+ years is not existent. 

I am excited with the new regulations.