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Okay, so I’m what you’d call “unique”. I am a very mobile user and also very disorganized, so I need tools to prop me up. But, over the years, the hard lessons of early-adopter victimization have saltied me to the gimmickry of high-tech, especially in the PDA world where I have been lured countless times and have subsequently filled several Dairyland milk crates with Sync cables, PDAs, and other useless bulk — I am reminded of this pain every time I move to a new place.

I have had 3 or 4 different generations of the PALM PDA, starting with the very first one; waaay back I have been the owner of an Apple Newton and a beta tester of the MagicCap from General Magic. I have also owned an SMS-capable phone for the last 3 years (at least) and a WAP phone for 8 months.

Most recently I have destroyed or lost two consecutive RIM Blackberry 950s. To anyone who knows me well, this means that I use those most frequently (you always, after all, hurt the ones you love). So clearly the Killer App for me is wireless email. I’d also love to do instant messaging, just so I can keep up with the Joneses. But the RIM 950 and 957 have, for me, two distinct problems:

– No MacOS connectivity software (I have rejoined the desperate, seething hordes of Macaholics) – A shitty, shitty (did I say shitty?) address book that won’t sync to anything

So, periodically, as I am wont to do, I set out this evening to see if the PDA world had caught up to my needs.

The spec for me is simple:

– Sync to an address book on my Powerbook so that Eudora and my PDA share the same data. – Give me wireless email on the go. – Have a keyboard.

http://www.palm.com My eye was caught by the Palm Vx with a specifically styled and shaped Minstrel modem, albeit briefly. I had thought for a moment that you could actually use AOL Instant Messenger and Buddy List from it, and you can — but only with a landline modem connection. What gives? Also, while the form factor is super-cool (easily the best) the external keyboard you have to get so that you can type is big and ugly. Oh… and the price is a whopping $600. No way San Jose.

http://www.handspring.com Next, I flopped back to the Handspring. They’ve got some great deals ranging from $200-$400 for the Visor, and there’s a $99 deal on the Minstrel right now. Kick-ass! Well, the more I looked into it, the more I realized one key thing that will be the Visor’s undoing: The Visor is a shell — a house for mobile applications. This is great, but what if you want to do more than one at a time? For example, while I’m using my GPS to find a Mercedes Dealership in Beverly Hills, why should I have to remove my wireless email device? What if someone’s trying to reach me? UGH. Sorry, there, Sunnyvale.

http://www.blackberry.com So off we go back to the RIM 957. The new form factor rocks and rolls… this time they’ve got it right (though I wish it ran Palm OS AND had the keyboard), with a bigger screen that does graphics.

They’re all the rage here in Hollywood, by the way, because they’re big and they allow you to be cool in restaurants in a subtle-but-still-obnoxious way. You can pretend you’re a VC and your date is pitching you her latest business plan, and like most VC pitches you both go home, empty-handed and feeling like the other is a dolt because you spent the evening banging out emails to HomeGrocer.com customer service.

http://www.motorola.com/GSS/CSG/direct_pagers/T900/ Next, I dropped in on the Motorola T900 2-Way Email Pager. Everybody I know in the wacky consumer wireless products space is fawning over this thing these days. My friend Mike calls this the “RIM Killer”, but I think he’s wrong. Motorola is clearly thinking with their Paging hats on this device — it’s a stand-alone device, with no PC Sync capabilities and very lightweight address book.

This will be a successful product in migrating the barrios into email-happiness (bloods and cryps will now be able to email each other locations for potential bust-ups) but will not reach a huge market and will definitely NOT solve my particular problem.

http://www5.compaq.com/products/quickspecs/10632_na/10632_na.html Alas, the iPaq. With a derivative name and a similarly derivative Windows OS, need I say more? Definitely high on the cool factor, though, with lots of features, colour.. and the winner of hype-of-the-month club for sure. You can get Omnisky for the iPaq as well as other solutions, however it suffers my scorn for being in the same blast-radius as the Handspring and Palm as far as features. And expensive! Blech.

Conclusions:

What nobody (but me) understands is that this device is supposed to be much more than a personal organizer, or an email client, or a pager, or a mobile applications device. It’s the convergence of all of these things and in many respects of ME: the offloading of menial tasks in communications and organization normally stored in my failing brain, now handled by a convenient, wireless connected device. Web browsing is interesting. Allowing me to do things easily and from anywhere that I hate doing is great.

But who wants to shove cartridges in and out of the rear expansion slot every time they “change” modes? What is this, a frickin’ Game Boy? The wireless email application, and instant messaging for that matter, relies on a persistent data connection to be useful — it doesn’t want to be “turned off”. If you can’t keep it in there 24-7 because you have to remove the expansion card in order to run your PDA-based business accounting software, what’s the point? From a user behaviour perspective, it’s just as unreliable as regular email on a PC.

With all of the work that has gone into PDAs, nobody’s managed to hit it yet. Too much focus on the Personal and the Digital, and not enough on the Assistant.

The verdict? Maybe if I didn’t have a Mac I’d be all over the 957. I might give up on that cause and get one anyway, and pray that someone comes along and solves my sync problem.

-Ian.