Yes, you make perfect sense, but when it comes to iTunes, iPods, etc., I'm not up to speed (never owned an iPod or MP3 player), and my laptop doesn't have an optical drive; albeit a nice piece of machinery: a Sony Vaio G1, not officially available for the US market, which I've had since '07 and which, since intro, has remained the lightest full size notebook standing, at 1.89 lbs due its use of full carbon fiber casing and SSD (thought you'd might appreciate this, since you seem to be gadget-wise).
This is what I'm referring to, but I'd appreciate any superior / further info / a known workable solution for converting:
http://www.e90post.com/forums/showthread.php?t=279294
http://www.e90post.com/forums/showthread.php?t=337241