Hi, Clinton
My experience has been very similar to Bruce's experience. Last Friday I had an operational Outlook application under Mavericks that I use at work. I installed Yosemite (over the top of Mavericks) on the weekend. Came back to work on Monday and have since
found it impossible to get a connection to the Exchange server.
I don't experience the "missing main window" problem. I just can't get a connection to the server.
I get continuous popups of the following dialog.

Checking "Always use my response for this server" appears to have no effect: the dialog box comes back. If I try using curl on the URL listed in the dialog box I get a "600" error, but then so does my colleague running Maverick - but his Outlook works.
I have tried setting up the account in Apple Mail (by the way, I agree with you about Apple Mail), but this does not work either, with very little (none) feedback.
I have no idea what to do now. Outlook doesn't work: web access to Outlook does work (but is very inconvenient). I'm not sure who to "blame" here (apart from myself for not reading this forum before upgrading to Yosemite ;)). Though, I suspect it's Microsoft's
problem for not keeping up with changes in the new release of Mac OS X - I mean Yosemite was only in public beta for how long? months?.
I have tried "delete .plist, move identity files, reboot, ..." recommendations: didn't work. I've tried the "kill the database daemon" recommendation: didn't work.
Outlook is the only application of the many I have on this machine that doesn't work.
This is very frustrating.
Cheers, S t u a r t .