I'm having the exect same issue and have been combing the web trying to find a work around. I've reinstalled Office, rebuilt my Font Book and rebuilt my Outlook database...nothing works...I'm also have an issue with my desktop clock every time my macbook goes to sleep it stops keeping proper time. Funny thing though the time is exactly right when I got to "Date & Time" in preferences...sure could use some good idea on the Outlook fix...I can live with a screwed up clock but I live for Outlook.
I'm used to using Office and Outlook (on windows, at work). I got MS Office for Mac which includes Outlook to make it easier to share back and forth with work environment. as I recall, I could do more rich text editing, see images embedded in the emails etc more extensively in Outlook for Mac than the native Mac Mail app. and I think that Mac Mail wouldn't let me create personal folders - but I may be remembering it wrong. In any case, things may have evolved over the last few years. so I will check out native Mail to see if it would make sense to switch.
I can say that Office for Mac 2010 completely sucked ! but 2011 version was much better, especially Excel and Word. Even today , there are weird things with Office for Mac 2011, like icon for increasing/decreasing font sizes - the small "A" icon is for increasing font size, and the large "A" icon is for decreasing - wtf !
Outlook 2011 is more complicated than Mail, Address Book and Calendar. Using it might depend on what other machines you want to sync with. The best thing about Outlook 2011 is that it usually comes with Word and Excel, both of which are waaaaaaay better than Pages and Numbers for any work more advanced than really basic.