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These are some troubleshooting steps for Outlook crashing.
How to add a shared calendar in outlook
Schedule a meeting using Microsoft FindTime in Outlook
How to remove delegate access in Outlook 365 for Mac or Windows
Steps to share your Outlook calendar with another user.
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.