Keeping them straight is easy because all of the platforms offer the ability to synchronize and automatically populate both with each other and google calendar. 

So I'm on to my next deal. put a calendar reminder to check in with him once a month and see if he (or the probate process) may be ready at that time.

All the calendars are synced but I check them each to make sure there is no double booking after I get a reservation on one platform.Like Julie said, create your systems. 

Utilizing some of the technological resources out there (shared calendars, project status updates, clear email chains) to keep all team members on the same page for this project has been key.

I spell all of this out in the lease:Funds Collected on or Before Lease Signing:The following funds are due on or before the signing of this lease agreement unless otherwise agreed to in writing:First Month’s Rent: $1000Security Deposit: $1000Pet Fee: $NA Last Month’s Rent: $NATotal Due: $2000Second Month’s Rent (Pro-Rated Amount): $500  (Due Oct 1)     Yes, this does require a little more thought upfront than just having the rent due on whatever calendar day they move in but once you do it a few times it's not bad and definitely worth the effort to keep everyone on the same schedule. 

It definitely would help to have a person/service that automatically imports your airbnb/vrbo calendar, so they know when each turnover is without you having to call each time.

Did it specifically say seven calendar days?

All leases are one year and then renew month to month with two full calendar months notice.

We have it on the events calendar here.

Then look and see what their rates are and how full their calendar is.