Via mail, I got this question:

I have Entourage EWS running now off Exchange Server 2010 and will be upgrading to Outlook. Do you recommend:
a) doing a fresh download of all mail and other data from the server when setting up Outlook, or
b) importing the data from Entourage into Outlook locally?

With a fresh download, you’re starting off with a clean slate.  This is important for someone like me who’s been using Entourage since 2004, since gunk can build up in your database.  But, with an import, you get the goodness of keeping all of your local data.  Since I have been using Entourage for years, and at one point I had a teensy Exchange account size limit, I’ve got lots upon lots of local data.

With every release, I’ve gotten into the habit of starting off with a clean slate.  For this release, that means that I first saved out all of my local mail (that’s the only local data that I have: all of my contacts, calendar, and so on live in Exchange).  I let Outlook start off with a clean slate, download my mail from Exchange and from my IMAP accounts, and then imported the local data.

To do this, in Entourage for Web Services, I saved all my local mail folders by dragging them out of Entourage and onto my desktop.  That creates .mbox files, which can then be imported into Outlook (as well as any other mail client which supports .mbox files, which is most of them).  I don’t have any other local data other than mail, but I’d do the same if I did have local contacts, calendar, notes, or tasks.

Then, after Outlook had downloaded all of my Exchange and IMAP data, I made sure that it would show my local data.  Go into the Preferences, then select General, and make sure that the box next to “Hide On My Computer folders” is not checked.  Then, I dragged those .mbox files into Outlook.

In my opinion, that’s the best of both worlds: I start fresh and still get to keep my reams and reams of local data.