Actually I think the OP might be onto something. I've used iTunes for years for both music and podcasts. In all that time, I'm not sure I've ever just bought something, downloaded it and listened to it. There's always an obscene number of hoops to jump through.
iTunes needs to update first ... whoops! The update broke it!
iTunes needs you to verify your paypal account. You do so and iTunes doesn't acknowledge it. Verify your paypal account again and again in an infinite loop.
iTunes isn't convinced the person who logged in with your details, your password and from the same machine as always is really you.
iPod wasn't recognised. Take it out and plug it back in. iPod was recognised but we've wiped everything off it. Better download it all again.
iPod has low battery. A moment later it's on full battery, then half battery, then full battery ... then it runs out completely in the middle of an audiobook and didn't save your place.
I can fully believe this is the work of the Devil. By the time I've got the damn thing working, I'm about ready to head out and murder the first person I see.
I am in general happy with Apple (we are an Apple household) BUT I fully agree iTunes is s**t. They've lost the plot, through greed, basically.
It started as a reasonable way of handling music files, input from a variety of sources, and I was able to use it for that, and sort and retrieve them. But it has subsequently morphed into a tool for Apple to
sell you music - and geared only for pop music, at that. It is almost impossible now to work out how to upload music from my CD collection and then retrieve it. The file structure seems impenetrably obscure and unintuitive. And the last time I tried to buy something from iTunes, it irretrievably scrambled the tracks which, for classical music, ruins it completely. (Imagine a version of Bach's B Minor Mass in which you first of all get the 3rd movement of the Gloria, followed by the first of the Agnus Dei and then the second of the Sanctus. I mean, WTF?) I actually complained and eventually got my money back.
I note on the latest version of Mac OS (Catalina) they have now stopped calling it "iTunes" and call it "Music" instead. But I'm not going to touch it with a barge pole.