
iTunes should be a web app...
Never used it on Linux (for obvious reasons) and my experience with it on my parent's windows machines lead me to suggest that the 90s called and want their idea of a dedicated and closed software interface to external hardware back. It does really, really, really suck and I'm not usually a man for repeated modifiers.
Proper portable media players are the ones you can just drag and drop to - you know, the ones that comply with widely accepted open standards. And proper media sales operations don't require that you need to download 80megs of cruft before you start giving them money. There's these brilliant things called websites...
In years to come historians will marvel at our collective willingness to put up with Apple's closed ecosystem nonsense just for a few glossy surfaces and fancy UI innovations. And before I get labelled as a hater I would happily buy DRM-free music from Apple (or anyone else) if they showed any inclination to let me do so without taking over my computer.