I'm not a big fan of iTunes but I see a trend that the Windows users complain the most. So, although the program is just subpar on MacOS, it seems to be really bad on Windows. Basically I think that they started out with the (correct) Apple thinking that it needs to be as simple as possible and usable without understanding what's technically happening. But they somehow didn't find the right metaphor for the program. And after that they just added feature after feature, redesigning the user interface whenever they had a new idea about making it more user friendly, but actually making it more awkward. The Music App on iPhone is the victim of agile development. I'm sure that the app on iOS 10 is a complete redevelopment, and the product owner never went through the trouble of checking what the iOS 9 or iOS 8 app actually did. I'm still missing features in the iOS 10 version that were present in iOS 9 and long before that. Or maybe my memory is blurred, and I'm having visions of a great past that never was. Whatever.