They could stay there for a one bed, $1000+ per night for an island view or stay in my 2 BD / 2 BA with spectacular views.  

In which case, if he sets up the state LLC correctly, and depending on what documents are available for public viewing, he would be able to pull it off no? 

So really there are two points of view here.

This approach reveals more about the tenant’s behavior and reliability beyond simple yes or no answers.Check multiple referencesContact at least two previous landlords for a comprehensive view of the tenant’s rental history.

Again if they balk at that, I view it as a red flag.

But how much more viewing would I get for the Zillow fee?

Your marketing is inadequate.Getting views but no bites? 

If you're wanting to put it into real estate, then choose a custodian like Advanta, Provident, Nu-View, Quest, etc that will allow you to truly "self-direct".

@Stuart Udis Do you think you could help @Max Bellinowith a very high level (helicopter view) of what you think should be good to start with?

I always view midterm renters people who want all the amenities.