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If your issue is whether or not the 2 different Outlooks will sync with each other, that's not a problem. Some of the elements from the newer version may not sync with the older version, but they're usually not important (I think 2003 has the ability to have a picture associated with a contact, something that's not supported in previous versions).
If your issue is in "which" contacts to sync with your new job, you can setup Categories in Outlook, and then tell each ActiveSync which of these categories you want to sync.
For example, if you don't want your family members loaded into your new Outlook, make sure they all have a category, and then tell ActiveSync, NOT to sync that category of contacts (Options>Contacts>Settings). Same thing with Calendar.
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