Hi Scott,
I understand that the Outlook for Mac 2015 crashed. I would like to explain that it is a pure client related issue.
Because this kind of issue is related to the Outlook client while our forum focuses on Office 365 Online services with limited resources on the Outlook for Mac client questions, I recommend you post this question in the Outlook for Mac forum below for professional suggestions:
http://answers.microsoft.com/en-us/mac/forum/macoutlook?sort=lastreplydate&dir=desc&tab=Threads&status=&mod=&modAge=&advFil=&postedAfter=&postedBefore=&threadType=All&tm=1405580497543
Your understanding is appreciated.
Regards,
Xinyu