Hi Damien,
Happy New Year.
I noticed a Christmas song that I had purchased in iTunes over 10 plus years which plays fine in iTunes does not synch or migrate over to Audirvana after several attempts using the second method for synching in Audirvana. I have also deleted and re-downloaded said song on the iTunes side and tried the re-synch on Audirvana with no positive results.
Regards,
Tommy R.