I agree with the comments above.Most important is a fully furnished, comfortable property with the basic amenities: coffee, teas, functional kitchen (all utensils, spices, cooking and baking, etc.)

My vision is for this meetup to be informal and organic.

I don't like the search function.

All told, cash flow will be a function of your down payment and your management of the property.FL tourism continues to flourish. 

Today’s buyers want spaces that flow naturally and maintain functionality.

They are functional while frustrating. 

A San Diego host I know switched their lead photo between their pool and a cozy firepit setup depending on the time of year - it kept the listing fresh and boosted engagement year-round.Capture Functional LuxuryGuests love spaces that solve problems while feeling high-end.

They do have a property management function that maybe could assist with this?

Finally, who have you interacted with from management and what, in your mind, would make communication, functional?

Quote from @Trent Reeve: well, a company would have to 50 states and build in integration functionality for 50 different systems.