Okay, so here's what I did, let me know if this will hopefully work.

I moved my actual iTunes library data (the entire Music/iTunes folder)
over to the WHS network share.

I then deleted it from the Mac and started up iTunes while holding down
the option key.  I pointed iTunes to the library over on the network
share.

This all worked!

Then I installed the iTunes updater plugin and reconfigured Squeezebox
Server to use iTunes and iTunes updater.  I pointed it to the Music
Library.XML file on the network share.

So now my Mac and the WHS have access to the same library data.  The
only source of confusion for me is whether the files the Mac uses and
the files the WHS/Windows instances use are the same.

I believe Mac uses the Library.XML file and Windows tries to use the
iTunes Music Library.XML file and I'm not sure if the two files will
really stay in sync.


-- 
jmpage2
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