I like too much music, and iTunes has a hard time keeping up, as does the phone, old phone, usb sticks, work laptop, ... I download just over 2 albums a week, and rate new songs before transfer to listeners (phone, ...)
Backups to net disk at home, and replace the HD in jab.ook every couple of years. Considering cloud, and dev server. (Pro tip: always buy a second copy of a HD: "Well we could've restored it if we had parts") Home network is shite, but I'm promised 4G in a couple of years. Distribution from jab.ook is via USB.
I listen to music tracks randomly from the phone
In the 11 months leading down from January 2012 I lost over 36 kg to arrive at my goal weight yesterday: 77.7kg. I did this by weighing myself daily, and using myfitnesspal.com to record pretty much every calorie that I ate. I did not really "follow a diet", just educated myself about the calorie content of what I typically ate, and preferred those with lower calories. It was also important to become aware of how I was eating, especially to notice that I did not eat because I was hungry. Now the second half: maintain 77.7 for the next year.