Ok,
So, to answer my own post... 

It seems that the 'Extract iTunes Artwork' option just doesn't work. 
After a bit of playing around I have found the following approach to
work...

1. Disable 'Extract iTunes Artwork' in the squeeze box options.

2. Ensure all artwork is added to EACH TRACK in iTunes. 
Need to be careful about this, as some of the albums had artwork
associated with just some of the tracks per album, and iTunes can use
this for all of the album, but not squeeze box. Need to ensure that each
track has the artwork.

3. Use the 'Re-Embed' script from Doug Scripts to ensure the album art
is embed directly into each file metadata and not just the iTunes DB.
http://dougscripts.com/itunes/scripts/ss.php?sp=reembedartwork.
Need to monitor the Re-Embed script when it runs to ensure it doesnt
fail part of the way through.

4. Clear squeezebox cache and rescan full library. 

I hope this helps someone. Its not too fast but at least it works!

Conor


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