Can't sync contacts properly

I want to sync my contacts with Blackberry Desktop Manager, but when I go to sync it, it starts to sync, but then stops. There's no error, it syncs as though there are no contacts. "Please wait a moment," then a ding sound.
I also have three different contact lists. One through Outlook, one through Outlook at the office, and one through Windows Mail. I want to consolidate the contacts into one big address book/contact list, avoiding duplicates if possible. How do I make this work?

Did you already try to reset the Sync history in iSync/Settings on your Mac?

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