Yes, if I understand you correctly. Second part it would appear you are about to find out for yourself. Enjoy.
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Newly - this is important!
To achieve the quality that is possible, you must set up iTunes correctly for the rip.
Make sure that Crossfade, Sound Enhancer and Sound Check are NOT selected
Under Preferences/Playback/Import Settings
select Apple Lossless with Error Correction On - this is the highest quality possibly with iTunes
Nothing to do with quality but I suggest you select the boxes "Keep iTunes Music folder organized" and "Copy files to iTunes Music Folder" This will keep all your files in one place which makes back up a lot easier
Finally, after the DAC is plugged in to the USB cable - you need to go in Applications/Utility/Audio MIDI SetUp and set the pulldowns as follows:
Default Output - pick the name of the device or the DAC
System Output - pick the name of the device or the DAC
Under Audio Output/Source select Digital Out
Format 44.1 2ch-16 bit
Then push play