Recently I was asked the question, "Why is it that you hate the iPhone?" The surprising thing about that question is that I don’t hate the iPhone at all. But I can see why so many of you would think I do.

After all, given that I own multiple companies with promiment presence in the Mac and Apple space, you would almost expect me to have one. I almost expect me to have one. But I don’t. And when colleagues ask me if they should get one, more often than not I find myself talking them out of it.

There are a few reasons for this which I’d like to explain.

Jaded Nerd
I’ve been in this technology business a long time. My early days were spent chasing down all the problems with early adopters trying to use the Next Big Thing, only to find myself on the bleeding razor’s edge of something that never worked right. So the build-up to the iPhone definitely brought back all the hell I went through with people blindly buying over-hyped products only to find that they weren’t reliable.

The iPhone was over-hyped, for sure, but it’s NOT unreliable. Apple made certain that it works properly. To do this, though, they had to limit its capabilities out of the box lest some piece of application interoperability that no one thought to test crashed and burned all of the device’s mystique.

It’s Not a Smartphone
Of all the people I’ve talked to and reviews I’ve read, the folks who love the iPhone are those who were on the fence about whether or not they might need a "smartphone" in the first place. Once they got the iPhone, they loved all the new functionality they had.

Going from a RAZR to an iPhone has got to be a wonderful experience. Going from a Treo or a BlackBerry to it ... not so much.

I’ve been a Treo guy for well-over two years and I have yet to see one committed BlackBerry, Treo, or Windows Mobile smartphone user adopt the iPhone in full without adding the caveat of compromise. It’s because they know what they’re missing. All that third-party support, all of the ability to customize, and heck, the beauty of copy and paste are unavailable on the iPhone! Yes, the iPhone runs OS X and that in and of itself had us all excited at first. But the (current) implementation thereof is quite limited. Sure, you can hack the heck out of it, and thank goodness for that, but "corporate America" isn’t going to adopt something they have to hack to get it to work with their systems. All the true smartphones out there warmly welcome third-party applications to be added to them to allow the device to really shine.

Boiling it down: What serious business user could consider using a "smartphone" that has no ToDo list and only syncs with iCal? Not me.

I’m Chicken
Don’t get me wrong -- I do have a bit of technolust for the device. I’ve spent a not-quite-so-trivial amount of time considering how I could go about making the iPhone work for me. But the end result is a plan so full of compromises and "temporary" workarounds in hopes of better functionality down the road that I’m scared to death to pull that trigger. I am ridiculously happy with my Treo 650. It syncs with Now Up-To-Date, my calendar of choice, I can archive my SMS with Missing Sync (another great third-party app), and I can sync with Yojimbo where I keep all of my notes for various projects. Best of all, I use a third-party IMAP email client, ChatterEmail, that affords me true e-mail nirvana: I have the same, fully-synced, inbox on my phone that I have on my desk at home and at work. If I reply to a message on my Treo and then file it, back at my desk the message is in the archive and the reply is in my sent folder. And it fully (and truly) supports IMAP IDLE for those times when I really want instant notification of incoming messages... from any compliant IMAP server.

You’re all thinking: yeah, well, the iPhone can do most of that. And you’re right, but most is not what I’m after. I have all of it already! Would I like the iPhone’s web browser? You bet your bottom I would. But, to me, that’s not worth the tradeoffs.

Instead of calling it a smartphone, the iPhone is a cell phone combined with an iPod. And if I were a RAZR user, I bet I would have loved getting one but, for now, I’ll stick with what I’ve got. I have a feeling you folks will let me know when they’ve got the kinks worked out.

Dave Hamilton is President and CEO of The Mac Observer, Inc and BackBeat Media, and producer and co-host of TMO’s Mac Geek Gab Podcast. He has worked in the computer industry for 15 years, doing time as a consultant, trainer, network engineer, webmaster, and programmer. In his earlier consulting days, he worked on the Mac, all the various Windows flavors, BeOS, a few brands of Unix, and it is rumored he once saw an OS/2 machine in action. Before that he ran some of the earliest Bulletin Board systems, but most of the charges have since been dropped, and not even the FBI requests that he check in more than twice a year.

Dave maintains his blog at DaveTheNerd.com