A mishmash of experiences and suggestions.

If you want to set up Outlook 2011 to work with a Gmail account, I recommend How To Wrangle Outlook 2011 To Work With Gmail. I reckon it saved me a lot of time and headscratching.

And if you then want to move old emails stored on your computer into Gmail folders, that's just a drag-and-drop operation from the existing folder to the appropriate folder (label) in your Gmail account. My experience is that you don't want to move too many messages at a time (about a few hundred seems OK), partly because of the amount of time it takes but also because of the risk of things going wrong. So consider using categories to keep track of what's been copied from a particular folder and what hasn't.

A related problem is that the first several times I created a new folder in my Gmail account from Outlook, everything went well. But now every time I try to do that, the result is "An unknown error has occurred in Outlook. The IMAP folder could not be created." So I have to create the folder from within the Gmail web interface. Not a huge problem, but more effort than should be necessary.

(If you've found a good way of reducing the number of messages that Gmail incorrectly categorises as spam, please pass on the method.)

The main thing that precipitated my move from Office 2008 to 2011 was the way Entourage had taken to crashing on me. Sadly, Outlook is far from 100% reliable. Here's hoping that Microsoft will address stability issues sooner rather than later. And there's a good number of users hanging out for calendar synchronisation too.

Did you know about the advanced typography features in Word 2011? Check out Bring Your Words to Life with Advanced Typography from Microsoft's Office for Mac team. There's some cool stuff to be put to work, especially if you like ligatures and variant letter forms.

Something I'd overlooked until today in Word until today is File>Share>Email (as HTML) and >Email (as Attachment). Although I don't really approve of HTML email, I can see why you might want to use Word to create the text rather than Outlook.