OK, that's what I thought you'd see -- those files are all floating, which is why you're seeing them change ownership when you run with and without sudo.
What's weird is that chowning them didn't chown -- which leads me to believe you didn't do it quite right.
So, do the following:
sudo chown -R phil:staff /Volumes/Music/iTunes/*
sudo chown -R phil:staff /Volumes/Music\ Backup/iTunes/*
Then, restart and give the backup another try.
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--Dave Nanian
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