I didn't think converting my Outlook email would be such a hassle. After much casting about for solutions including the purchase of O2M from Little Machines and Emailchemy from Weird Kid Software, I will detail what worked for me.

O2M did a good job converting my Contacts and Calendar over to Address Book and iCal. Mail was not handled quite so well. However, for $10, it's hard to complain. Emailchemy is the only tool I could find that could directly convert an Outlook .PST file to Mail.app format. Unfortunately, I had hundreds of messages convert with no subject, dates, recipients, etc.

What I eventually discovered is that the best way to convert is as follows:

1. Open Outlook Express (or Windows Mail on Vista) and import all of your Outlook items.
2. Dig around in the Outlook Express options looking for the message store location. It will be something like C:\Documents and Settings\tlindsey\Local Settings\Application Data\Identities\{5246B4AF-59D3-45E3-90FF-BC8F6E2732D4}\Microsoft\Outlook Express.
3. Open the message store location and copy these files over to your Mac.
4. Run Emailchemy and choose to convert Outlook Express to Mac OS X Mail.
5. Open Mail.app and choose Import Mailboxes and select the newly converted email folder.
6. You should now have a folder in Mail.app called "Imported" which will contain your mail.

So far, using this method, all of my messages have come across intact.