I guess if I was to decribe my email setup in the terms of a relationship, then "it's complicated" would be an apt description.
One major issue that I have is Outlooks Autodiscover feature which is supposed to help Outlook discover the correct Exchange servers to connect to.
This works fine if I am connected to my work LAN or VPN, but if I want to look at my offline cached email, Outlook insists on connecting me to my organisations main email servers. Problem is, my email account is not there, and I have no valid Exchange login for there, so Outlook continually prompts me for credentials which will never work, oh, and the button to "never ask for these credentials again" doesn't work either.
Best or only option I have found for stopping this prompt is to enter a fake autodiscover address into my local hosts file. I enter the following line:
127.0.0.1 autodiscover autodiscover.myworkdomain.com
You'll have to replace "myworkdomain.com" with whatever matches your work email address.
How does that work for you?