I'm finally upgrading from OE to Outlook on the advice of Brian Tinkler of the Wisconsin .NET User Group (among many others over the past few years). The main reason that I stuck with/chose OE over Outlook was that Outlook97 didn't have an easy way to select which FROM address to use for emails, and I was frequently switching between several POP3 accounts from several organizations. OE had a nifty little dropdown, Outlook didn't. Outlook97 combined with Visual Studio 1.0 also tended to totally slow down my P2-300 laptop that I had a few years back...
So, I'm installing the Beta that came with my MSDN subscription and hoping that it is pretty stable. If not, I'll blame Brian since he told me to use it. It has a cool business contact manager thing that he says is nice, and with the amount of emails I deal with on a daily basis (and the number that have been slipping through the cracks lately), I'm hoping that helps.
Another issue that has been nagging me for some time now is spam. I've been debating signing up with a service like SpamArrest for a while now, but before shelling out money and forcing everyone I know to deal with this thing, I thought I would try another free solution that I've heard great things about, SpamBayes. Unfortunately, SpamBayes is a plugin for Outlook and wouldn't do squat with Outlook Express - another reason for me to switch.
While I'm writing about email clients, let me plug ABF Outlook Express Backup. This product rules for anybody using OE. It backs up messages, address book, favorites, rules, everything. Why OE doesn't come with such a utility is beyond me, but for $30 this thing is worth every cent. I backed up my OE stuff before beginning my Outlook upgrade and the resulting file was about 950mb. So it can definitely handle LARGE amounts of mail (can you tell I'm on a bunch of listservs and I never delete anything but spam?).
So, as you might imagine if you've done this process, with that much mail in OE, it is taking hours for Outlook to import all my stuff from OE. I have no idea how much longer it's going to take, but once I get it set up, install the business contact thingy, the spambayes thingy, and use it for a bit, I'll post back here about my experience.
[Listening To: Chevelle - Send the Pain Below]