I am very interested in using Pure Music to play HiRez DSD and FLAC files, while using iTunes in the way I've always used it to sort and organize music. I was wondering if anyone knows how tracks added to iTunes by Pure Music sync to an iPod classic, if at all? Obviously the iPod only supports WAV/AIFF/ALAC at a max of 16 bit 48kHz - but I am given to understand Pure Music works by creating a hybrid DSD/ALAC or FLAC/ALAC file for use with iTunes anyway? If this is the case, is iTunes smart enough to sync the ALAC part of the file only to a connected iPod classic? 
 
I would love to start buying DSD music online for home listening, and then put ALAC versions of those files on my iPod classic for in the car and on the go. Is this something Pure Music could handle automatically for me?
 
For bonus points: What about iTunes Match? That doesn't support anything over 44.1KHz - again, would it pick up the ALAC "chunk" of the hybrid file created by Pure Music?