Some may feel that I have a love-hate relationship with the iPhone, given the lengthy criticisms I've penned about this device over the past two years. Fair enough. I certainly do have a complex relationship with the iPhone, which is as Windows-antagonistic as any Apple technology and yet functional in ways that other smart phones have yet to emulate to any meaningful degree. That uniqueness makes the iPhone less like technology and more like a living thing: You love it despite its flaws, maybe even because of its flaws. I mean, the thing just doesn't care. It almost makes you want it more.

Silly pseudo-psychiatry aside, there are some realities of life that are intruding into this decision. In my case, specifically, there are two. First, I really need to get going with Windows Mobile, what with Microsoft shipping at least three major updates this year: My Phone, Windows Mobile Marketplace, and Windows Mobile 6.5 (see my preview). Secondly, the iPhone, as I've endlessly complained, is simply too expensive.

So, what does this actually mean?

First of all, I still believe that the iPhone is absolutely terrific technology and the best smart phone solution out there, by far. There is nothing that touches it. This is particularly true if you bypass Apple's bogus Windows sync software (and Mobile Me) completely and use something like Google Gmail Contacts/Calendar, where you can sync to the device over the air (OTA). The iPhone's expandability, App Store content, and iPod functionality really put it over the top. Used to its potential, the iPhone is absolutely amazing.

Second, I fully intend to keep using the iPhone--or perhaps an iPod touch--and will continue bringing this device with me when I travel. It's just that I won't have access to AT&T's cellular networks, which will be limiting in some ways but liberating in others. One of the huge advantages of the iPhone is its excellent Mail application, which facilitates the quick "triaging" (as I think of it as email). Standing in line in a grocery store, at an airport, or wherever, I can quickly delete or move unwanted email, ensuring that when I do sit down in front of a PC, I only have a handful of emails to actually deal with. In a pinch, I can also use the iPhone to respond to very important emails. It's great functionality, but going forward I'll only be able to do this when connected to a Wi-Fi network.

Let's do some math to see why this might actually work out. Currently, I pay AT&T $89.79 a month for the privilege of using an iPhone. This bill includes the cheapest possible phone plan ($39.99), the cheapest possible data plan ($30), the lowest-end SMS plan ($5), international roaming ($5.99, which is something most iPhone users won't get), plus various fees and taxes. The lowest possible iPhone bill would thus be about $78.80, taking out SMS and international roaming.

That's possibly acceptable if you use the phone and data a lot. But I don't. Out of the 450 minutes allotted to me last month, I used 43 minutes, and I have 4,993 night/weekend minutes rolled over. (Some of these minutes are deducted monthly as well; it doesn't matter.) My data usage minutes are currently unavailable (because we traveled internationally last month), but the last bill I looked at noted I had used up about 45 Mb of data transfer. Not much.

Looking a full year of usage, $78.80 x 12 is $945.60. The data plan portion of that is $360. If I were to travel for work once a month and access airport-based Wi-Fi each time (thus enabling me to check email on the device), at an average cost of $10, that would set me back $120.00, or about 1/3 the cost of the iPhone data plan alone. My guess is that I wouldn't pay for Wi-Fi even that frequently.

Put simply, the iPhone doesn't justify the cost, for me. (It may for you.) And this isn't just the iPhone. Any smart phone data plan wouldn't make sense for me.

There are questions.

I need to cancel my iPhone and AT&T will charge some sort of fee for that. I'm not looking forward to this conversation.

I need to purchase a Windows Mobile 6.1 device, possibly for use as a phone, but without a data plan (and with Wi-Fi, so I can at least test data services at home). This will be expensive: Smart phones are subsidized for people who get 2 year contracts with a data plan. Non-subsidized smart phones can cost as much as $500. This, plus the iPhone cancellation fee, could literally wipe out whatever savings I'd otherwise see by dropping the iPhone. There aren't too many choices, when you filter the list down to Windows Mobile 6.1 plus Wi-Fi, and those choices vary by wireless carrier.

I could potentially move to a month-by-month plan, using a low-end cellphone as my wife does. In fact, she does this because she doesn't use the phone that much either, and she's saving about $30 a month now, compared to what she was paying before.

Multiple devices stink. I will still keep an iPhone/iPod touch around for the apps, PIM sync, and for future testing. But I need a Windows Mobile phone, also for testing. And a cell phone, whatever that may be, for occasional phone calls while traveling. Staying with AT&T may have some financial benefit, but God I hate their network and would love to get back to Verizon.

In the end, I suppose even breaking even financially will make sense, as I do need to do a lot of Windows Mobile work this year. I'd like it to work out better than that, however.

Stay tuned. I'm very curious to see how this all works out.