Hi John,
Regarding these two issue, I’d like to confirm the following information to identify whether the issues relate to Office application or SharePoint Online.
1. Could you please check the version of your Office 2011 and Mac OS X? If the Office 2011 is not the latest version, please update it.
2. Does this issue happen to a specific library or all the libraries in your SharePoint Online site?
3. If we use Document Connection to connect to SkyDrive Pro, whether will this issue occur?
For the second question, only Outlook for Windows uses the .msg format. If you have many messages to read in Outlook for Mac, then copy them into a PST file first. You can import the PST file into Outlook for Mac.
Thanks,
August