There is a nice meetup list on the Straight Up Chicago Investor's Podcast website here: Chicago Real Estate Investor Meetups (straightupchicagoinvestor.com)Hey John, I will check out that meetup list and get one on my calendar.

We use Hospitable.com as our PMS and they make calendar integration and payment through stripe easy enough. 

I'm seeing a lot of open calendars on most comps in my area.

Kyle hosts a good monthly meetup at https://calendar.google.com/calendar/event?

I have not heard good things about either.Vrbo and Airbnb (preference to Vrbo) should keep your calendar full.

It integrates with the AirBnB calendar and immediately sends guests an email right after booking is confirmed.

Look how full their calendars are to get an idea on occupancy, then check nightly prices at different times of the year.

Any additional amount you purchased for would get new calendar for 27.5 years (if residential).

You can, if you prefer not to go through a service like that, but there are a lot of things in the backend you'd need to have in place that these platforms provide; like calendar syncing, guest messaging, etc.

Make sure the theme can work with widgets for calendars, payments, reservations and that they can link up with AirBNB and VRBO API's to match calendar hits.There is just too much to really cover here.