Once the road expansion is complete for the the new amphitheater the calendar should be released of events. 

Check their calendars for occupancy.

Study your neighbors calendars.

You'll need:- A good task list program (accessible on desktop and mobile)- A good calendar (accessible on desktop and mobile)- An email scheduler (RightInbox is one I like for Gmail)- An expense management tool (Expensify is the best I have used)- File storage for EVERYTHING (GDrive is my choice)Definitely recommend getting on top of those, first and foremost.

How do their calendars look?

Link all the calendars to keep up to date.That way if someone needs the extra space, they can rent both.

From my perspective, YP does everything I want it to do and has an easy interface and a very nice calendar which shows you some useful data on it besides just that there is a booking and what platform it was on.  

A short-term rental:Host's primary residenceOwner-occupied during rentalGuests have restricted use of homeNo limit on frequency of rentals per calendar yearRentals cannot exceed 30 consecutive nightsA vacation rental:Host's primary residenceOwner is not on the premises during rentalGuests have exclusive use of entire home (host and other guests not present)Limit of 90 night cumulatively per calendar year*Rentals cannot exceed 30 consecutive nights*A host may apply for an exemption to the 90-night vacation rental restriction here if their employer, or their spouse or domestic partner’s employer, requires them to work outside of the District for more than 90 days cumulatively in any calendar year.

There are a lot of tools that help -- Turno for coordinating with cleaners, Pricelabs for dynamic pricing, Guesty for calendar management.

We know how to kill it with that crowd.Outside of statistical research, we found SO many airbnb and vrbo listings in the area that are absolute dog vomit properties that had, and continue to have, full calendars at good nightly rates.