Some carriers won't allow insured to be a trust, so in that case do it in your company name with trust as additional insured.

Hi Matthew, I work for a property managment company in Milwaukee that assists many out of state investors.

If they think they have an "Airbnb" Unless they own the publicly traded company, then they only have a STR, or a vacation rental if they have a nice place/location.

Some car companies don't allow transfers of their cars shortly after they are released.

Hi Karen, Have you tried reaching out to any other local investors or property management companies? 

The macroeconomics look so good for this market - population is growing, job growth is growing, and so many companies moving and developing here.

I recommend having a pricing software (pricelabs perhaps). 

When we first went live (with a property management company), most of our bookings came from AirBnb.

I know out here on the West coast with our digitalized title plants that each title company has it would be a matter of a few clicks for customer service department to transmit a copy of the mortgage to me..

Just because another real estate investor has success working with a particular company or person does not mean you'll have the same experience.