Apple needs to get its head in the cloud

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When those who follow these sorts of things speak of Apple and its strengths and weaknesses, the S and Ws often break down along these lines—Strengths: Just about everything; Weaknesses: The Web.

Though some may argue with the first, very few will contend that Apple’s done a bang-up job on the latter. Apple’s history in Internet services not concerned with clicking a button to buy something has been littered with failures and half-hearted forays—eWorld,, Ping, iWeb, and iTools/.Mac/MobileMe. And the imperfect results of these efforts have led some to claim that Apple “doesn’t get” the Web. And while that may be true, I think it’s also true that Apple hasn’t had a compelling need to.

Setting aside eWorld, which launched during the dark days when Apple couldn’t navigate its way across a crowded room, much less an Internet service, these other services were largely convenience features—the “wouldn’t it be nice” add-ons that could make a user’s life a little easier. A bit of Internet storage here, some light social networking there, and a place to publish your movies and pictures over thataway. But they've hardly been a smashing success. Google Docs is better than for collaborative work. Ping is too limited and cumbersome. iWeb was a nice idea but Apple didn’t nurture it. And MobileMe is a disjointed hodgepodge of services that don’t tell a cohesive story.

But with however-many-umpteen billions in the bank and an astonishing streak of successes, Apple hasn’t really had to worry about its Web strategy. I believe those days are coming to an end. And for two reasons: Syncing and media.

It’s no secret that Apple has moved into mobile in a huge way. Yet, surprisingly, when it comes to syncing files and data, Apple’s mobile devices are at their clumsiest when not physically attached to a computer. For instance, can I see a show of hands from those who’ve turned to storing files they need in their Dropbox so that they can later import them into an app like Documents to Go for later work on their iPad? (Or, worse yet, failed to put them in their Dropbox and frantically called home asking their mate to e-mail the necessary files because Back to My Mac doesn’t work at the hotel.) Similarly, how many have found their iOS devices, .me account, and Macs loaded with duplicate contacts, calendars, and bookmarks because they guessed wrong in Apple’s convoluted syncing game?

Syncing, in its current state, is a mess. And it’s a mess that Apple can’t afford to ignore. If we’re increasingly going to carry around these extensions of our electronic lives in the form of iOS devices, the fodder for those devices—the files and data we live by—must be easy to synchronize and move around, without the need for wires. (And I mean Mom-and-Dad Easy, not Your-Typical-Geek Easy.)

Additionally, we need a structure that allows the synchronizing of the vast majority of our files—not just contacts, calendars, notes, and bookmarks, but also word processing, presentation, spreadsheet, and graphics files. If there’s truly “an app for that,” that app needs seamless wireless two-way synchronization with a compatible computer-based application. Throw in a Web-based application for collaboration, and you’ve got something better still.

And then there’s media and the need for wires. Apple’s aware of the media I’ve purchased and rented from the iTunes Store. Should I really have to attach a cable from my iPhone to my Mac in order to move some of that media between the two? Wouldn’t it be far simpler if, while connected to Wi-Fi, I launched the iPod app, saw a list of all my purchased media, and then tapped a song or video to have it stream to my iPhone?

All this leads to iCloud, Apple’s rumored Web enterprise. What might iCloud bring to make the critics smack their heads, realizing that rather than being tone-deaf to the Web, Apple was simply waiting for the opportune moment to show how it should really be done? Let me take a crack at it.

Intelligent syncing: Currently, on your Mac, you can muck around with syncing in the MobileMe system preference, in iTunes, in iCal, and in Address Book. On iOS devices, you find syncing options in the Mail, Contacts, Calendars area. Add Google syncing and you’re looking at yet another sticky layer. Enough already.

Turning to the future, when you set up a new iOS device or install the next version of the Mac OS, you see a single “Choose the content you’d like to sync” option. Tick off such options as Contacts, Calendars, Bookmarks, and iWork documents, and the appropriate items are synced to iCloud. Through a little checksum magic and intelligent sleuthing, iCloud recognizes duplicates and either deletes them, merges them (in the case of contacts), or provide access to multiple instances using a Lion-like Versions feature. Your Apple ID identifies you, and iCloud takes care of the housekeeping so that regardless of how you access your data—iOS device, Website, or computer—you see the same stuff.

For extra security, equip iCloud with a Time Machine-like interface so that you can roll back through time to recover data that has been overwritten, altered, or replaced. And while you’re focusing on extras, toss in an “I have a Google account” option that also syncs your data with that service.

Collaboration: One of Apple’s greatest talents is taking flawed technology and making it great. Much as many people find Google Docs useful, I’m going to lump it in with lumpy technology. The interface is anything but attractive, it’s not mom-and-pop friendly, and it can be confusing when multiple people are banging away on the same document.

Apple could do this better by making an iWork suite that’s iCloud-friendly. Open a Pages doc on your Mac or iPad, and invite two other people to work on it with you. Those people could be working on their Macs, the Web, or their iPad, and the look of the application they’re using would be nearly identical. When you need to communicate via something other than text, call up a video window where you can see and talk to each other. (Let’s call it FaceTime with a business bent.)

A presence: At the risk of urging on Apple in a futile attempt to compete with Facebook, it would be nice if iCloud provided you with a unified Web presence—one where you can post pictures, movies, personal updates, blogs, podcasts; share documents; and do a little social networking. The company has made attempts with iTools, .Mac’s HomePage, iWeb, and MobileMe galleries, but none were easy or complete enough. At the very least Apple could create a presence for you that’s more attractive and less invasive than Facebook’s and, at best, a compelling window to all aspects of your life—work as well as play.

All media, all the time: I’ve pretty well described the first part of the dream—make purchased media available for streaming. To expand on that dream, do so without requiring that users upload their media to a server. Put a system in place that verifies you’ve actually purchased the stuff and then simply stream the content that’s been verified. The media companies are likely hostile to such an idea, but Apple has some muscle in that world.

Regrettably you can’t extend that dream to include all the media you have, because Apple has no way of proving that you legitimately own it. But suppose you take ownership out of the equation. For a reasonable monthly fee, make everything in the iTunes Store streamable. Even make it portable by allowing downloads (which, naturally, expire if you stop paying). Yes, it’s that dirty word—Subscription—but it needn’t be a requirement but rather a concierge service available to those who find such a thing attractive.

This is as far as I’m managed to stick my head into the cloud. If you had the power to make Apple’s online efforts truly useful, what would you do?

[Christopher Breen is a senior editor for Macworld.]

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