Hi Jeffmattyz,
Based on your description, it seems that you want the following in the communication site in SharePoint Online.
- You want each person in your organization to only view their own events and add the events to their calendar
in Outlook.
- Only the training department members can add the users’ events in the calendar.
If yes, you may need to create each calendar list for each person to add their schedual events and set the unique
permission for the list for only the specific user to view their schedual events and sync the calendar list to Outlook 2016.
The Office 365 group calendar is for Office 365 group members to see the shared events and add new events. So
each one in the Office 365 group member have the permissions to edit the calendar. For the calendar list in the communication site in SharePoint Online, you can add all events for all users in one calendar and set different views to show different events for
user. However, users with the Read permissions can still switch views to see other events. When users use the Connect to Outlook option to sync the calendar list to their Outlook 2016 clients, they can still see all events nomatter related to them or unrelated
to them.
So for the scenario in your organization, the better way is to create each calendar list for each person to
add their schedual events and set the unique permission for the list for only the specific user to view their schedual events and sync the calendar list to Outlook 2016. I know that it is time-consuming for you to deploy it, but this may be the only out-of-the-box
way in SharePoint Online now. Moreover, I also suggest you post a new thread on our
MSDN
forum which is a specific forum for SharePoint development solutions to see if the engineers there can have a development solutions for your scenarios in your environment.
Thanks for your understanding.
Cliff