I feel your pain, Julien.
As you know, we're all set up on Apple here, from our phones to all our computers to Apple TV. And I must say that when I did make the switch from PC to Mac a few years back, it was almost like a revelation.
Then Steve Jobs died. And things started taking a strange turn. And not for the better.
At first I didn't really notice much, since I didn't upgrade to the newer OS versions Apple. There were minor but nevertheless very annoying changes to iTunes, like the removal of cover flow, which I loved and which helped make iTunes stand out of the crowd.
But then those changes for worst seemed to take place at a faster rate. And I can tell you that in the last few months, I've rarely spent more than 2 or 3 days without cursing Jobs successor, Tim Cooks.
The latest versions of iTunes have even the biggest Apple fans pissed off.
Me, I can't seem to add an album to my iPhone w/o having 3/4 of the music that's already on my iPhone randomly deleted. I get error messages saying that the files cannot be played on this iPhone, which is ridiculous as they were playing fine 2 seconds earlier.
So every time I want to put new music on it I have to erase everything first and then re-add it. Which takes forever. And is so frustrating.
My iPhone is an older 32 GB model, meaning that I can't put my whole library on it. Nevertheless, for whatever reason, at random times, it will switch from listing the stuff that is actually on my iPhone to the content of my entire external iTune library. Not just what I bought in the iTune store, but every single CD that I've ripped and that sits on an external HD. So I end up having to navigate through hundreds of artists and albums, duplicates and all, on that tiny iPhone screen to get to the albums that are actually playable on the phone. And I have yet to find why this happens and how I can fix it. It seems to fix itself after a few days.
The latest version of iTunes also seems to have done away with a couple of options and changed the default settings - for exemple, iTunes now loops albums by default, which annoys me to no end. And I can't seem to find where they buried the option... The running time of the album also seems to have been removed - that's information I was actually using and that's often how I pick the albums I listen to in the gym, to time my workout.
All this for what? To get me to buy into streaming and connect with artists and socialize and rate albums and whatnot. I have to jump through hoops and click 3 times as many buttons to get access to a third of the functionality. Me I just want to playback albums I paid for.
I tell you - if I could, I'd buy a bunch go pre-2012 Mac running Snow Leopard and an older version of iTunes, store them somewhere, and those would be the computers I'd be using for the rest of my life.
At this time, I don't know what to do. I'm not moving back to PC - Microsoft does a fine job of following in Apple's footsteps, anyway, and there are still tons of things which I prefer on Mac, including Logic.
I guess I'll simply have to learn and live with/manage my frustration.
But it's not just Apple, anyway. Even my bank's web site was recently re-designed and made more tablet friendly I suppose, trading functionality and readability for "modern design".
Lowest common denominator, always.