Computer Audio

I think you can install the Sony software and point it to the iTunes library - it would then transfer the files to the Sony player itself.

You are faced with one of the highest switching costs in computer audio: re-ripping CDs. It's a pain in the rear!

Not sure if you are aware iTunes is not very good in audiophile terms both for playback and ripping. I assume the Sony box you mention is the higher end DSD unit that has been much talked about. I understand that box is capable of very good sound, but of course you need to feed it good files.

Think about gradually re-ripping your CDs. The best approach I know of, and pretty future-proof so this doesn't happen again, is described in computeraudiophile.com "Guide to Ripping CDs". It's a great tutorial based on dBpoweramp. I follow it to a t and works great. In one shot, I rip the CDs to wav and flac and aiff, and the software checks online a database to confirm the copy of your CDs digitally matches other same CDs - so you know is a perfect digital copy.

I know re-ripping 700 CDs is a rather daunting task. But it's worth to do this over time and have an uncompressed library. I believe iTunes compresses everything and you don't have a way of verifying how good the copy was, let alone moving to a different software given the proprietary format.

I hope this helps despite not answering directly your question.

Cheers!

iTunes doesn't provide an error log but if you have no issues, the rips should be bit perfect as long as you rip to you use Apple Lossless, WAV or AIFF.

And iTunes sounds very good with a plug in like Audirvana Plus/Amarra/PureMusic.