Contacts will refuse to sync to iPod

For some unknown reason I am unable to sync my contacts from Outlook 2000 to the contacts on my iPod Video. When I try to check sync contacts, iTunes crashes. However, when I check the option for calenders, it says that it cannot sync. Is Outlook 2000 too old for it to sync? I would change it back to the standard Address Book program but I am not allowed to because the only way to change the option is by checking the box to sync which I obviously cannot. Help would be appreciated.

Im having the same problem here on my Dads PC running Windows XP (poor guy...)
When I try to get his machine to synch to the iPod Nano I just gave him iTunes crashes when I try to get it to synch to his Contacts.
What's the dillyo?

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