[kcmac]

A known issue with iSync is that it will only sync the first address for a contact if you have two labeled the same. (ie. 2 work addresses within the same contact.)

Apple says to make sure the one you want to sync is listed first.

It does not appear that you can drag and drop these addresses to change their order. Does anyone know a simple way to change the order vs. deleting and then retyping?

[MickS]

You could always export the addresses as vCards into a file, edit them in a text editor and re-import.

This might by quicker than deleting and re-typing in AddressBook