With each new product that Apple announces, including the revamped Apple TV and the new Ping social network, Steve Jobs reveals a little bit more of his plan to dominate the media universe. But I can summarize that plan’s fatal flaw in one word: iTunes.

Don’t get me wrong. I think Apple’s hardware is unbeatable, and my admiration for it has only grown since I got my first iPod back in 2003. My home/office is virtually an outpost of the Apple Store: with the exception of the TV, the videogame console, and the coffeemaker, almost every device in my house is an iGadget of some kind. The operating systems that power my Apple devices are pretty good, too. I love OS X and I’m very glad that Xconomy is a mostly Mac shop. On the mobile side, Android is impressive, but iOS is the slickest and most user-friendly mobile operating system out there, in my judgment.

But there’s one piece of the Appleverse that I’ve always detested, and that’s the desktop version of iTunes. The ugly duckling of the iFamily, this program is hard to understand, hard to use, inelegant, and ill-behaved—in short, the very opposite of most other Apple products. I dread booting it up every day, yet I can’t sidestep it. What makes iTunes’ deficiencies so infuriating is that the program is indispensable: it’s the nerve center that stores all of your Apple-related media content, mediates all of your Apple-related purchases, and connects all of your Apple devices.

The rollout of iTunes 10, the latest “upgrade” to this nearly 10-year-old program, was one of the two centerpieces of Steve Jobs’ keynote talk on Wednesday, the other being Apple TV, of which I’ll say more in a moment. And the big new feature of iTunes 10 is Ping—a Facebook-like social network designed to help users discover music by seeing what their friends are buying for their iPods.

I’ve been playing with Ping, and it seems to have most of the features you’d expect of a media-centric social network circa 2010—profiles, friending, news feeds, comments. Plus, of course, you can easily preview or buy the songs or albums mentioned in your friends’ news feeds. It’s easy to see how Apple might expand Ping beyond music to facilitate conversations around media of all sorts, including movies, books, and mobile apps.

That said, Ping has some serious limitations that, to me, are symptomatic of the larger problems with iTunes. For example, there’s no integration with Facebook or even with your contact lists, so it’s virtually impossible to find real-world friends to connect with. For a social networking tool, this is a bit of a problem. (Kara Swisher at AllThingsD grilled Steve Jobs on this very issue, and his suggestion for finding friends was to “type their names into search or send them emails inviting them to join.”)

And there’s an even bigger issue: Adding a social networking interface, on top of all of iTunes’ other functions, is like grafting another limb to the forehead of an octopus. It’s just too much.

Few people may remember this far back, but iTunes predates even the iPod. It started out in early 2001 as nothing more than a program for ripping CDs and playing the resulting MP3s from your computer. (It was based on … Next Page »

Wade Roush is a freelance science and technology journalist and the producer and host of the podcast Soonish. Follow @soonishpodcast

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