We allowed ourselves ample time to close, but with the way the calendar fell there was multiple holidays in between the expected date of closing.

I would log in to airbnb as a traveler and see what how many properties are listed, their listing price, and view their calendar to see how booked they are.

If you use Vrbo/Airbnb are you just going to block out the calendar that you don't own?

I have an ownerrez widget setup so that I can accept reservations, real time, and cross link the calendars so it blocks on AirBnB and VRBO nearly instantly. 

We share a calendar that is updated consistently and we both make sure to prioritize time together. 

The first person that uttered those words never owned watch, or used a calendar. 

Some states require the lease to end at the end of a calendar month, but most states allow you to end on any day of the month as long as notice is given the proper number of days in advance.

Seller shall deliver at seller's expense:(1) Not later than (5) calendar days after acceptance of this Contract by Buyer and Seller.

When you want to utilize your STR, you just block out those dates with the manager and they block those on the calendars.  

Just go through all AirBNB and VRBO/HomeAway listings that are similar and get a gander at their calendars.