Hi Rick,
Thanks for your detailed information. Now I understand you have set up your Exchange Online account on Outlook 2011, and you want to sync all the calendars from other kind of accounts to Office 365 calendar via the Sync tab on Outlook 2011.
I’ve done a lots of test, and didn’t find a way to do this. The Sync tab on Outlook 2011 can only sync the data on the mailbox on Outlook clients to and from mailbox server, and cannot sync the calendars between different mailboxes. For this feature, you may need to contact Apple support for further help. Although, we can sync all the different calendars to Office 365 account on Outlook client, this changes won’t be synced to Exchange Online, so you can only view these calendars on Outlook client.
For this feature you are concerning, we welcome you submit feedback here for the further improvement of our product. If the service is requested frequently, the product team may include it in the future releases.
Best Regards,
Vivian Wang