Man, Apple is really good at building phones and software for it, but it seems like they're dreadful at anything music related.

I haven't had the disprivilege of using Apple Music, but I've lost many a nights sleep over iTunes. I remember using it a long time ago, like pre original iPod Touch time, and everything actually worked pretty decently. Updates weren't horrible. iTunes was snappy and did a lot of useful things. It was so good, in fact, that my family didn't even own an Apple product until many years after we started using iTunes. We mainly used it to buy music and to burn and write CDs. It was great.

Over time, it started getting worse. Updates started becoming frequent, so much that every time I loaded the thing, there would be an update waiting for me. iTunes started to become less responsive. It used to be a little sluggish when starting up, but it got to the point that I could almost make a sandwich before the thing would load. I had an MP3 player, but eventually upgraded to an iPod, which was a mistake, because now I was forced to use iTunes. In reality, adding a couple of songs should have taken a few minutes at most, but Apple was having none of that. I had to open it, wait for it to load, tell the thing "No, I don't want to download an update", search through the clunky (Slow computer didn't help at all) iTunes store, find and buy the right song, then go through and drag the songs onto the iPod (which was nice and simple. I know I could have synced it, but it was a family account , so that was too complex for my 8 year old brain). It wasn't preferable or fast, but it still worked good enough that it was a minor issue.

Eventually, I upgraded to an iPod touch, then an iPhone, and the problems got worse. I was finally old enough to buy my own music, so I set up my own account. I figured, since my computer had the songs already purchased and downloaded, then I could simply get away with adding the files to my library and then putting them on my phone. iTunes noticed and gave me an "Aww, hell no." It would tell me that I didn't own that music and needed to choose between the libraries. For the rest of my ownership of Apple products, my two accounts fought over each other over the rights to my device. If I didn't pay enough attention when adding music, one account would take over and nuke most of the music on my device. Every now and then, I'd do a sync and come back to like 20 songs on my phone, because the old account somehow did something to delete the rest. If I had one account, everything would have been fine, but having, like, 5 songs from another account was enough to make adding a couple of songs from the computer a nightmare.

That's doing it manually. Every now and then, I'd get defaulted back to some setting that would just delete everything off my phone or add back a bunch of apps that I deleted. I never really sat down and figured all the settings out, because I didn't want to get intimate with iTunes - I just wanted to sync some damn music to my phone.