Hi Brian,
Thanks for providing all the information requested.
According to the test result, it seems that the username or password is incorrect. Please check them when you configuring your Office 365 in Outlook 2011 for Mac.
I’ve checked your DNS records and found that the CNAME record for Autodiscover service, which is needed, is not pointed to autodiscover.outlook.com and also the MX record is not pointed to Office 365. Could you confirm whether you have any local deployment for Office 365?
If not, please edit to point the CNAME record for Autodiscover to autodiscover.outlook.com at your DNS hosting provider. Wait for up to 72 hours and then try to configure your Office 365 account on your Mac again to see if it works. You also need to point the MX record to Office 365 to get mail service work.
Meanwhile, could you confirm whether you are using parallel systems by saying “I can get my office 365 account to work in outlook 2011 on my lenovo laptop using windows 8”? Do you use your Lenovo laptop in a different network?
Thanks,
Lee Li