Find a way to sync without using Outlook and LINK....
If you are using a POP/IMAP account with limited online storage (webhost)..... time to upgrade. It might cost you $5 a month, but it will save you in headaches.
If you have an online solution with plenty of storage, they should have the ability to either use IMAP or better yet ActiveSync - Gmail, Yahoo, Outlook.com.... You can have an online email service like one of these, receive and send you existing email address - look at adding an alias.
That way all syncing is instantaneous, no more LINK can not connect issue, no more duplication issues.....