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Yo,
I don't know about Tasks, but there should be a long way around for getting appointments and contacts from your desktop to your Axim.
Apparently WM2003 supports "vCard and vCal files" - usually sent as email attachments, representing a single outlook Contact or Calendar Appointment, respectively. So, if you have WM2003, and a desktop version of Outlook that supports vCard & vCal, then export each of your contacts and appointments (including those Red Sox games) on your desktop to these types of files, transfer them to your Axim, and open them with explorer. They should be imported into your pocket outlook applications.
I have never done this, but it is a theoretically solution for you to try. Let us know if it works!
-B
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