This way they can block off the dates they wish to use the property in the calendar and it will be available to them.

I am not sure if you can see calendars or not, but check.

When I look at calendars in Elijay, they look sparse.

Check out listings there over the next few months and see how booked their calendars are.  

To answer your questions * You can look at sites like airbnb, vrbo, airdna, etc to see what options in your desired areas are booking for by clicking through their calendar.

Make sure to have the window when this is open on your calendar each year, so you don't forget to ask for it. 

-Calendar sync (most do this now across the channels)-Automation of messages (obviously I feel like they all do this now but some better than others, from what I have read smartbnb is the best in this regard but that is about all it does, that I want at least.)

If I wanted to talk with him, I had to go to his online calendar and schedule an appointment. 

The calendar gets kept in Trello and I have card templates with things to do and reports to run, which have links back to the instructions for completing them in Confluence, and then links to any of the needed Google Drive files.

Variety of topics with different experts.West DFW REI Group- https://www.westdfwreigroup.com/ Check their online calendar for meeting times.