This is the first post in a little series about my experiences with the conversion from PC to Mac.
Outlook
For exporting Outlook uses .pst files whereas Apple uses .mbox files for email, .vcf files for contacts and .ics files for calendar items. Unfortunately the different Microsoft and Apple file types are not interchangeable.
Browsing the net for a solution I quickly discovered that a free AND smooth conversion from Outlook to Apple Mail is not possible.
Probably the cheapest solution is to download O2M from Little Machines; it costs only 10 bucks. There are other options out there, but they’re all more expensive, so why bother if the end result is the same?
For now O2M only supports U.S./English versions of Windows and Outlook, so that is something to keep in mind. You can select which folders to add and for your calendar you can select a certain date range.
Before I set O2M to use, I decided that now was the time to clean up my email and I archived everything from before January this year.
Then I let the program do its job and copied the results to an external HD to be able to move it all to my new iMac.

Easier than making Apple pie!
[screenshot courtesy littlemachines.com]