Syncing iPod Nano with Outlook 2003

Hi folks! I'm hoping someone here can help me. I have 2 8 gig 3rd generation nanos (mine and the wifes) which are way cool. I use to have a HP iPaq handheld which I used to play music and carry my scedule and contacts on. However ther is very little support for this old device and I went to the iPod thinking it wouls eassily sync to Outlook 2003 on my HP Vista machine. I worked at first although it woulds only sync select few appointments on my calendar but my contacts were initialy OK. I got it to function OK on both iPods as my wife and I need to know each other's scedules and we use the same contact list.
But recently I have been having issues with the sync as it routinely gives the error message: "iTunes failed to sync with Outlook calendars (or contacts) please log out of windows and log back in" When I log back on my calendar and contacts lus is gone on one of the iPods and will not sync back short on resetting the unit. So far the list will remain on my wifes unit but I am SOL. Anny advice would be appreciated

This isn't going to help but I want to add that my 3G Nano has similar issues. I use Outlook 2007 and it syncs just fine, no errors. Problem is that none of my contacts nor calendar items are sync'd. I have selected Outlook in iTunes CONTACTS tab as the source to sync from too.

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