By looking at properties in cities you are interested in, you can see demand and what people paid (look at your competition's calendar and see how often they were booked or what they were charging.)

I put it on my calendar to listen at that time.

@Jared Lichtin I wish I could make sometime between Oct 6-13 work for my calendar... darn!

Anytime I buy a foreclosure REO a good title company can usually get the bank to pay the entire calendar year’s tax for you...I have had good success with getting that approved. 

There is a calendar link on their main page. 

In that case, it would be easy to let the market determine how to fill your calendar. 

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This covers all marketing, guest communication up to the booking date and check-in as well as calendar maintenance.

Check out similar AirBnB postings and look at their calendars - are they booked up?

Typically insurance companies give you a calendar year to file a claim due to a storm/ act of God.