iTunes gets cloudy: Will a web-ified future save iTunes or kill it?

I'm not at all surprised that Apple's recent purchase of Lala Media, a previously-ignored music streaming outfit that likely would have flatlined otherwise, is already generating rumblings of impending major change to one of the most pivotal brands in its arsenal. While it was the iPod and iPhone devices that first established Apple's consumer product cred and later sealed its long-term position on the techno-cultural podium, it was iTunes that turned the process of buying, managing and consuming content from a chaotic mess into something that ultimately killed the local record store and permanently changed the entertainment landscape.

If only the world never changed

But nothing stays still for long, and as iTunes gets ready to celebrate its ninth birthday, its future is already being rewritten. And none too soon, because iTunes is badly in need of fixing. The package has virtually always been a pig. It's too large, unwieldy, and slow for its own good, and too quirky in day-to-day use. It sucks back system resources and forces users who like to work to music to make a tough call: iTunes, or work, but not both at the same time unless the performance goal is a 386 running WordPerfect circa 1989.

Apple has had eight major upgrade opportunities to get it right, and it's failed at every turn, adding features on top of an already rickety architecture and letting users on both Macs and Windows suffer the performance-sapping consequences. The interface, which has often served as a canvas for Apple's latest design theme, violates more usability principles than the dashboard of a first-generation Yugo.

The intent of iTunes is admirable, and it's been hugely successful largely because it's free and most folks consider it good enough. But it's about as far removed from Apple's simple-at-all-costs ethos as you can possibly get. It's time for Apple to get serious and apply the same design- and usage-led thinking to iTunes that it applies to everything else in its stable.

The shift is already underway

The timing for this transition is ideal given the current trend toward thinner, Web-based, mobile-friendly solutions that don't necessarily revolve around a computer. The concept of mobile devices tethered to desktop or laptop computers laden with entire libraries of purchased or downloaded music is increasingly seen as yesterday's model. Folks are getting tired of having to download something to a computer before syncing it to a mobile device. They're fed up with having to move gigabytes of content from one hard drive to another when they get a new machine.

Thanks to Google's ever expanding universe of Web-based services, consumers are also gradually becoming more comfortable moving some (not all, not yet, but getting there) of their precious data to the cloud. But it won't stop with productivity-related data. It's inevitable that music, video and related entertainment-focused content moves in that direction as well.

This transition toward cloud-based paradigms isn't just affecting the Microsofts of the world, and Apple knows it. And before a savvy web services outfit outflanks it with a cloud-focused content acquisition and management solution that out-iTunes iTunes, it looks like Apple's building a web-ified, wireless-driven solution of its own. Good on them. If you're listening, Mr. Jobs, here's my wish list:

• Make it work on any mobile device. I know it's tempting to give preference to the iPhone and iPod Touch crowd. Avoid the temptation at all costs. Remember how the original Mac-only iTunes exploded in popularity and cultural significance as soon as you released it for Windows? Keep the same strategy in mind this time out and make sure other major platforms like BlackBerry, Android and, yes, even Palm's webOs get to join the party. I know you've had fun blocking Palm devices from using iTunes, and I appreciate that you own the playground and want consumers to keep buying Apple-branded mobile devices. But at some point, this proprietary silliness has to end.
• Let me store everything in the cloud. Google's been hemming and hawing over its mythical Gdrive for longer than I wish to remember. Don't make the same mistake. Even if you have to cannibalize your .ME service, find a way to cost effectively let iTunes users stream their content online, again from any device. Whoever drives ubiquitous, cost effective, Web-based storage into the mainstream first, wins.
• Make the wireless carriers play ball. Strike a deal with them to introduce stream-friendly rate plans. AT&T will hate you, but none of this will ever fly if wireless consumers are worried about busting their measly 500 MB/month data allocations.
• Don't kill me with DRM. Don't make me jump through hoops to enjoy legitimately purchased content on a number of devices and/or platforms. Your decision to make the current iTunes DRM-free was a great one. Don't change direction now.
• Ignore protests from record labels and studios. They'll certainly howl with each inevitable step away from the models they've held near and dear for so long. Tough. After they failed to anticipate and respond to the realities of selling content in a broadband-driven Internet era, it fell to you, Apple, to introduce a model that worked well enough for everyone. Don't let them ruin the party now that content moves from download-and-install to cloud-based.

In the coming year, I expect this landscape to get a lot more convoluted than it already is, as players large and small maneuver around each other for position. As is often the case when markets move through historic inflection points, it isn't fully clear how all this will play out and who will be left standing when the dust settles. But the lessons that Apple taught the then-new online music market earlier this decade -- delete superfluous features, integrate the hardware, software and network, simplify the purchase experience -- continue to apply in today's vastly expanded multimedia market.

It'll be nice to finally have an iTunes delivery method that lives up to the promise and doesn't frustrate us with unchecked bloat, machine-tied inconvenience and interface-based gridlock in the process.

Carmi Levy is a Canadian-based independent technology analyst and journalist still trying to live down his past life leading help desks and managing projects for large financial services organizations. He comments extensively in a wide range of media, and works closely with clients to help them leverage technology and social media tools and processes to drive their business.