So I’m down in Chicago for the week (at The Drake!) for work and my colleague has an iphone. Some of you may remember my negative predictions when the iphone was first announced.

I have to admit that the iphone is one sexy beast. The screen is stunning and many of the features – such as surfing that web and looking at photos are amazingly clear and fluid. Possibly the coolest feature is how, as you rotate the phone, the image/screen always rotates with you so it remains in the upright position. That’s some clever work with the gyroscopes…

However, the one of the main concerns I flagged back in January was not assuaged. This being that the keyboard, because it is simply part of the screen, is not easy to use. Simply put, your thumb often presses the wrong key making one feel like the fat Homer Simpson in the episode where he needs the special “fat phone” because his fingers are too big to use a normal push button phone. Typing out email on the iphone will likely be too cumbersome and frustrating a process for the regular or business user to do regularly. More importantly, it pales in comparison to the Blackberry keyboard.

But my criticism pale in comparison to this increadibly thoughtful critique delivered by Peter S. Magnusson on Yahoo! (and sent to me by Rikia S.). Sadly, Magnusson’s comments are no longer available on Yahoo! so I’ve reposted them below. I wish I’d been half this clever:

I don’t think the iPhone fundamentally innovates over and above the existing offerings, in the manner that the iPod, the Macintosh, and the Apple II all did in their day. To the contrary, I find that the iPhone reveals that Mr. Jobs, and thus Apple, does not (yet) understand a paradigm of 21st-century computer usage.

At its heart, the iPhone is a projection of the original vision of bringing clunky desktop applications such as e-mail, contact databases, to-do lists, telephones, note taking, and Web browsing to the palm of your hand. Because that is essentially Jobs’s generation – transitioning from the mainframe office environment to the PC-based office – he can’t quite get rid of the notion that a mobile device is nothing but a really small personal computer.

Here’s my theory: Apple can only create really interesting products if Jobs understands the end-user. And Jobs does not understand the 21st-century user. In this century, people don’t send memos to each other.

Today, people chat; they blog; they share multimedia such as pictures, video, and audio; they debate (“flame”) each other on forums; they link with each other in intricate webs; they switch effortlessly between different electronic personae and avatars; they listen to Internet radio; they battle over reputation; they podcast; they do mash-ups; they vote on this, that, and the other; they argue on wiki discussion groups.

With the exception of a minimalist widget for text messaging, the iPhone does not have direct support for any of that. No support for sharing photos, no recording of podcasts, no text communities, no location awareness.

Without going through a computer with a cable, the iPhone doesn’t really communicate very much with anything.

In fact, when you want to communicate with somebody, the method (application) comes before the person. You first have to choose how to communicate (SMS, phone call, e-mail, Web service). Only then can you choose whom you want to talk to. That is a classical “code-centric” view of the world. Apple completely misses the opportunity to present text messaging, visual voice mail, and multimedia e-mails in a coherent view.

This is not a simple lack of features. This is not a “one-dot-oh” effect inherent in a brand-new product category. This is a fundamental lack of understanding of social networking.

What made the iPod a breakthrough product was that Jobs really knows music. He’s an artsy guy. He’s even known to have a really good musical ear. That’s why the iPod was awesome.

Social networking and Web 2.0 are apparently another matter. It’s a generational thing, I guess. Jobs is even older than I am, and I’m having a really hard time keeping up with the times. Plus he’s busier than I am.

What the iPhone should have done was put the social network front and center. It would happily invite the “play” aspect of modern computing, which is increasingly interacting with “work” – personal blogs morph to full-time jobs; YouTube postings lead to advertising agency job offers; entrepreneurial musings lead to investor contacts; and so forth. Chatting and sharing media should have direct support.

But Apple has a unique asset that may yet save the day: the sheer moral support it can draw from the tech community. This past weekend, for example, an entire impromptu developer conference was assembled with the sole purpose of “making the Web a better place for [the iPhone].” So, ironically, social networking technologists are busy arranging themselves such that Apple will, yes, recognize their significance and treat them as first-class citizens. It’s not too late.

I hope Apple listens.