Will Apple’s iCloud Finally Kill Off iTunes and End the Scourge of Sync? My Week in Apple Hell

Xconomy has been around for four years now (our birthday was June 27) and I used the same white plastic MacBook that whole time. It was a great little machine—but despite a memory upgrade, two battery transplants, and a new keyboard (I’m pretty hard on keyboards), it just wasn’t pulling its weight anymore. The OS was crashing daily, and important programs like Final Cut Pro wouldn’t run at all. So I upgraded last week to a beautiful new 13-inch MacBook Pro. I love the new machine, and I’m looking forward to trying Lion, the newest version of the Mac operating system, which could be released as soon as next week.

Unfortunately, this week I’ve been living in Apple hell, as I’ve struggled to sync the new MacBook with my other Apple devices—an iPhone 4 and an iPad 2. It’s been like bringing a new baby home to a house where there are already a couple of toddlers: they’ve been jealous and uncooperative every step of the way. I still don’t have my contacts, calendars, photos, and videos properly synced. In fact, somehow every device now has two copies of every appointment in my datebook. I had to spend an hour rebuilding all the app folders on my iPad after the new Mac scrambled and/or deleted most of them. And don’t even get me started on the photos and videos.

I blame it all on iTunes, which is the least appealing product Apple builds. (Well, MobileMe might have been worse, but Apple recently killed it.) It’s supposed to be the traffic cop in the Apple village, making sure that all of your songs, apps, photos, contacts, appointments, etc., get sent from your Mac or PC to the right personal devices. But the program has come under increasing strain of late, as Apple has introduced new gadgets that are themselves powerful multimedia computers. I now think of iTunes as Apple’s equivalent of the space shuttle—an aging workhorse that should have been put out to pasture years ago.

Steve Jobs himself put it perfectly during his keynote presentation at last month’s World Wide Developer Conference in San Francisco. The concept of synchronization has “broken down in the last few years,” Jobs said. Why? “Because the devices have changed. They now all have music, they now all have photos, they now all have video. I buy a song on my iPhone and I want to get that to my other devices—I have to sync my iPhone to my Mac and then sync my other devices to that Mac. But now they’ve deposited photos on the Mac, and I have to sync those, too. Keeping these devices in sync is driving us crazy.” Which is the same thing as saying that iTunes is driving us crazy.

I might have avoided my week of torture if only I’d been able to wait to upgrade to the new MacBook until this fall. That’s when Apple says it will introduce iCloud, a new system that will supposedly take over many of the functions of iTunes by copying all of your appointments, contacts, photos, videos, music, and app data to Apple’s data centers, then wirelessly and automatically syncing this data across all of your Apple devices.

If iCloud does everything Apple says it will do, it’s the beginning of the end of iTunes. (Developers already have access to a beta version of iCloud, but under an agreement that prohibits them from talking about it, so all we have to go on for now is what Apple presented at WWDC.) It’ll work like this: when you create a new appointment in iCal, the data will be wirelessly uploaded to Apple’s data centers, then wirelessly pushed back down to any other device registered to your Apple ID. The same goes for contacts and mail messages. In fact, Apple is reworking all of its major apps to work with iCloud. Books that you buy using iBooks on your iPad will automatically show up on your iPhone; videos and photos will go into a new “Photo Stream” mirrored on all of your devices, including your Mac or PC and your Apple TV. That will all sound familiar to users of existing cloud-based systems, such as Google Calendar, but for Apple it’s still a big step. “We are going to demote the PC to just be a device,” Jobs said. “We are going to move the digital hub, the center of your digital life, into the cloud.”

It can’t happen soon enough for me—or for a lot of other people. In a September 2010 column, I singled out iTunes as the weakest element in Apple’s growing ecosystem. “Apple’s strategy of using iTunes as the catch-all vehicle for every new feature and function that requires the intervention of a PC is starting to backfire,” I wrote. “It’s an extraordinarily creaky and unstable foundation upon which to build a new media empire.” That story attracted the third-largest number of reader comments in Xconomy’s history, with about half of respondents agreeing—as one reader put it—that “iTunes is pretty much made of fail these days.”

When you put the iCloud announcements at WWDC together with some of the other features that Apple said it’s building into Lion and iOS 5, it begins to look as if iTunes’ future role will be greatly diminished. The loudest applause during the WWDC keynote—aside from the welcome accorded to Jobs, who has been on medical leave—came in response to the announcement from Scott Forstall, Apple’s senior vice president of iOS software, that starting with iOS 5, iPhones and iPads will be “PC-free.” No longer will you need to plug your new iPhone or iPad into your computer to activate it when you get home. Everything will happen over the air. You can even throw away the little white USB cable: synchronization, daily backups, and software updates will now happen automatically over Wi-Fi. “Now, if you want to cut the cord, you can,” Forstall said.

What’s left for iTunes to do, if you don’t have to plug your iOS device into your computer every day to sync? Well, it will probably still be the place where you go on your computer to buy, download, and manage songs and other media; to rip or burn CDs; and to sync with your non-wireless Apple devices like the iPod shuffle, nano, and classic. In other words, it will be reduced to its pre-iPhone rank as a media management program—which is all it was meant to be in the first place.

As he described iCloud, Jobs came back again and again to one of his trademark phrases: “It just works.” I sure hope it does—but given Apple’s history with the synchronization issue, my bet is that the transition from iTunes to iCloud will be a bit stormy. After all, which copy of my contact list will be the one that makes it to Apple’s cloud: the real one on my iPhone, or the empty one on my new Mac, which so far refuses to sync properly? Will iCloud be smart enough not to turn my duplicate calendar entries turn into triplicates? What if everything works fine on the device side, but human error brings down Apple’s data center, the way it did for Amazon’s supposedly fail-safe EC2 computing cloud this April?

We’ll see about all this soon enough. I’m just saying that our flight to the cloud has barely left the ground, so there’s bound to be some early turbulence. But as long as Apple keeps iTunes off the plane, I’ll be happy.

Wade Roush is a contributing editor at Xconomy. Follow @wroush

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