I waited way too long to upgrade! My new system with Windows 7 and Outlook 2010 is working out great. So much of my time is spent in eMail and it was a bit tough to get used to the "ribbons" in Outlook, but so far so good. I ended up loading my "old" mail as archives so my new inbox would be completely free of clutter. All of my legacy emails are available when I need them, just not in my "inbox". One thing to look out for is that the latest version of Outook places the "pst" file in your Documents folder. This is a good place for it to be (people won't miss backing it up anymore), but if you were used to the old way of doing things where the pst was in some hidden folder, it takes a bit of getting used to.