Actually, I never use itune... too slow and can hang.
1. Android player (Except DX100) seldom can compete with i product.
can go check soomal.com...
2. you don't need to use itunes to add or change songs,
install a Flac, AAC...e.t.c. music apps such as Capriccio free music player
http://itunes.apple.com/us/app/capriccio-ultimate-music-player/id434828497?mt=8
Then use iFunBox to direct access your iPhone/ iPod
and change the songs on your device.
Very Fast.
3. or you go buy --> Samsung Galaxy SIII --> use OTG cable --> use Fiio E7 or E17 usb sound card --> output to your IEM.
I like my iPod Touch 4G (64G) or iPod Nano 6G--> DAC Alo Solo or Fostex HP-P1 --> Headamp Pico Slim or Corda Stepdance.
I sometimes also use Wifi drive to share music to my iPod Touch.
so I can expand to >64G and even connect to usb flash / usb drive anywhere.