Even though Apple’s new iTunes Match service, announced today during their 2011 WWDC Keynote, falls short of the potential that I see for music in the cloud (outlined in this post I wrote last month), I’m still generally encouraged by iCloud, the company’s enthusiastic new push into moving the computing experience off of our local hard drives. If nothing else, Steve Jobs’ tacit acknowledgment that its previous products in this arena have been less than dazzling is a satisfying new sign of self-awareness.

It’s no secret that MobileMe, the company’s current offering, as well as its predecessor .Mac, were both so underwhelming that they left most of their users only to despair that Apple truly didn’t understand the modern Internet at all.

The worst part of MobileMe though — indeed, the worst part of any of Apple’s cloud-based endeavors to date — was the company’s complete and utter unwillingness to acknowledge how bad their efforts were. For the most part, Apple remained impassively tight-lipped about poor performance, gaps in functionality and market-trailing features, all the while moving glacially slow (if at all) to make improvements. If over the past five or so years you were, like me, a user of any of either of these services, you probably felt — again like I did — that aside from paying your annual renewal fee, Apple pretty much didn’t care that you were a customer at all. Four years ago I wrote this rather snarky post that, while a bit sophomoric, still stands as a good summary of what it felt like.

Thankfully, in an offhand but very enlightening remark, Jobs spoke about the considerable and understandable skepticism generated by that approach, supposing that most of us would think “Why should I believe them? They’re the ones who brought me MobileMe.” Too right. Such an open admission is a huge step forward. I hope iCloud follows up with a truly substantive execution.

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Somehow I ended up creating multiple user accounts (under separate email addresses) over at TripIt (which is probably my favorite travel tool of the past decade). For a recent trip, I had stashed some data in one account and other bits in another. But thankfully TripIt made it relatively easy to consolidate these accounts together; after some simple email verification, I had a single user account that recognized both email addresses.

It made me wish that Apple would allow me to do the same thing, but alas they don’t. For a few years now, I’ve had two separate Appe IDs where I would very much like to have just one. Though I’ve tried to be conscientious about using only the one that I prefer, once in a while I’ll accidentally make purchases on the App Store or in iTunes with the wrong one. So now I have some digital purchases under one account and others under the other, which can make for a frustrating experience when I have to update or re-authorize any of them.

This seems especially egregious for Apple, as their suite of products creates so many opportunities — iTunes, MobileMe, iChat, FaceTime, even registering a new Mac, to name a few — where a user might inadvertently create multiple accounts. Allowing users to merge accounts, preferably through a simple, self-service Web tool, strikes me as a fundamental requirement for good customer management. This would seem especially true when your ecosystem is as large as Apple’s, when the company serves as the gateway to so many purchases, and when it stores so many credit card numbers.

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