Hi Ryan,
Thanks for your feedback and sharing your research on this issue.
You can refer to this article to know more detail about this fixed known issue:
Unable to edit Contacts, Appointments, Meetings, or Tasks within Outlook
And I would like to make a summary here so that more people can know more about this issue.
About the cause:The reason for this phenomenon is because some items contain internet
header information that causes Outlook to believe these items should not be editable. And it will affect not only contacts, appointments, meetings or tasks may also be involved.
About the fix:
a) Monthly Channel fix was released on April 29th in Version 1904 Build 11601.20144.
b) Semi Annual Channel will release ~May 14th in Version 1808 Build 10730.20340.
c) The fix for Outlook 2016, Outlook 2013, and Outlook 2010 (also known as perpetual versions) is planned for the August 13th 2019 Public Update.
About the workarounds:
Outlook users:
Create, view, and edit contacts and contact lists in Outlook.com
Office 365 users:
Create, view, and edit contacts and contact lists in Outlook on the web
Fix contacts in bulk:
Export all of your contacts, then import them so the internet headers are removed. This process marks the contacts as editable.
Thanks for your patience and feel sorry the inconvenience you have experienced.
Sincerely,
Shawn