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These are some troubleshooting steps for Outlook crashing.
How to remove delegate access in Outlook 365 for Mac or Windows
How to add a shared calendar in outlook
Steps to share your Outlook calendar with another user.
Schedule a meeting using Microsoft FindTime in Outlook
Delete appointment series on all accounts
How to request a new shared calendar
Refreshing Outlook should resync the emails and calendars that are not showing up properly. This would be the first step I would try in troubleshooting the issue.