Our organization just switched to O365 last week and all week long I have had to deal with connection issues from Outlook. Most of our users are using Outlook 2010, all patched up, Office 365 assistant has been run, profiles have been deleted and recreated. Outlook works for a few hours, or even a day, then I get calls from users where Outlook is not responding or stuck with "Trying to connect".
Autodiscover works just fine, be have TONS of bandwidth, and this is happening on a random group of users. This is NOT a client issue but VERY frustrating.
We went with O365 due to the Microsoft name and the stability of Exchange. Did I make the wrong choice?!?! I have a 30 day window to cancel but what a mess that will be....