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As I understand it, support for links (aliases) is not portable across all the OS that Calibre supports so any such change would not be accepted into the main Calibre release. Having said that if it could be done in a portable way it would definitely be a desirable enhancement.
Note, however, that calibre would not notice any changes done to the files by iTunes so even if an alias could be made to work the result may not be what you hoped for.
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