Illustrator Problem linking image

Problem: Working with Illustrator, when I link images twice or three times suddenly the link button does not respond. I have to close Illustrator and open it again and then I can use the link button again only  twice.
Any suggestion?
OS: OSX Yosemite v 10.10.1
Hardware: IMac 27" (2013) 3.4Ghz Intel Core i5
Software: Adobe Illustrator CC 2014

Hi Steve,
Thanks for the response.  First of all, you'll have to excuse me if I get a few points wrong, as I'm not too familiar with Illustrator.  However, in answer to your questions;
The layers panel is showing "<Linked File>" next to an empty white box.
Turning off preview does show the boxes you describe.
I've no idea how to go about checking if an image is beyond the mask bounds.  However, I've used the same image for testing across accounts and it displays fine on those that aren't having this issue.
Also, in the top left corner of Illustrator, the name os the linked image does display and the options available when clicking that do seem correct and working.  Relinking from there does nothing, but I can open the image for editing etc.  None of this helps in getting the image to display though.
As for the server side, we have always used a Mac server at the same version as the clients. 
Thanks,
Simon

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