In Part 1 of my Windows Mobile 6.5 review, I discussed the new features of Microsoft's latest smart phone operating system from a high level. Since then, I've used a couple of Windows Mobile 6.5-based smart phones as well as a Google Android-based Droid phone, which has caused me to rethink the notion of what a smart phone is circa 2009/2010. As I noted previously, Windows Mobile 6.5 isn't as lousy as you've been told. And when you compare the system and the devices based on this platform to the competition, you may be surprised to discover that Windows Mobile 6.5 holds up pretty well in the modern smart phone wars.

That said, it's no iPhone, and we should just air that out right away. In today's smart phone market, there is the iPhone and then there is everything else. Windows Mobile 6.5 is, however, roughly on par with Google Android 2, the system used by the Verizon Droid and numerous other smart phones. In fact, the similarities between Windows Mobile 6.5 and Android 2 are striking. Both offer similar user interfaces, though Android's is less elegant looking (if more consistent).

And both Windows Mobile and Android also offer something that isn't available on the iPhone: Multitasking. In fact, in all the belittling of Windows Mobile that occurs out there in the ill-informed blogosphere, the one fact that everyone seems to either forget or simply not know is that Windows Mobile has had multitasking since its inception in 1996 as Windows CE. Not interesting? Well consider this: The way multitasking works in Android is literally identical to how it works on Windows Mobile. That is, as apps are put aside, they stay in memory until that memory is needed, say by a foreground app.

This style of multitasking was derided publicly by Apple because it supposedly requires Windows Mobile users to manually manage applications by using yet another app to kill running processes. That's ridiculous--Windows Mobile manages the memory automatically--and, go figure, Android has the same kind of functionality.

If you're looking for something truly retarded, however, look no further than the iPhone, which allows only one application to run at a time. In other words, it works just like MS-DOS, circa 1983, except of course that it now supports cut and paste for minimal cross-application integration. The iPhone forces you to quit an application, go find another app, launch that, do something, quit that, and then go find the first application, if you want to move back and forth between apps. You know, just like DOS. Ah, the good old days.

That one bit of silliness aside, of course, the iPhone is clearly superior to both Windows Mobile 6.5 and Android 2. And when I say that Windows Mobile is no iPhone, I do mean just that. Here I'm referring to the full experience. This is where Android falls short too, for whatever that's worth, even more so that Windows Mobile. What the iPhone has that the other systems lack is elegance and simplicity. As noted above, these qualities sometimes do get in the way of the system's functionality. But come on. All you have to do is spend some time with the iPhone to understand why the trade-offs are almost universally worth it.

But back to Windows Mobile 6.5. What we've got here is the result of a decade's worth of resting on one's laurels. This is not a system that strikes any chords in the heart, and it's this lack of consumer excitement, I think, that has caused the blogosphere nimrods to condemn it prematurely to the dustbin of history. Indeed, what Microsoft did with Windows Mobile--or didn't do, I guess--nicely mirrors what it did earlier with Internet Explorer. Sans any serious competition, the company simply gave up. And as with IE, which was jumpstarted back into active development only after Firefox came along, so too did Windows Mobile see its comeuppance from an unexpected competitor, this time in the form of the iPhone.

To be fair to Microsoft and Windows Mobile though, the entire industry was slapped in the virtual face by Apple's innovative entry and now, almost three years after Apple announced its iPhone, we still don't see a single device that is capable of unseating this new dominant player. Yes, other phones sell better, especially overseas. But the iPhone has rewritten the definition of what a smart phone is--more than once, actually--and all the competition must follow now suit.

That definition is, I think, interesting because it determines what Windows Mobile is and what it should be, and these things don't always line up as they should. In the beginning of the smart phone era, a smart phone was simply a PDA wedded to a phone, and depending on how one approached these devices, that meant either taking a PDA (like a Windows Mobile/Pocket PC device, as Microsoft did) and adding phone capabilities, or doing the reverse. (Today's modern smart phone platforms, like iPhone and Android, are not bogged down by this historical legacy.)

A decade ago, then, PDA functionality became the baseline of what was considered a smart phone. Calendaring. Contacts management. Email. Basic web browsing. Media playback. A small set of useful utilities. A way to sync data between the device and the PC. Over time, this set of functionality evolved as these PDA/phones got Wi-Fi capabilities and wireless sync. Windows Mobile got a mobile version of Microsoft Office. Expectations evolved, if slowly.

This may sound similar to today's smart phones, but don't be fooled. The advent of push technologies changed the email/PIM functionality of a smart phone dramatically, as did wider access to more advanced email technologies like IMAP and Exchange.

It's hard to overstate how much the iPhone has changed things, generally raising the bar and redefining along the way what it is that a smart phone can do. The iPhone's iPod functionality is still unparalleled on other smart phones, for example. Its Safari web browser is desktop class, a phenomenon that is still reverberating throughout the industry as rivals try to catch up. The App Store is an unparalleled success, one that is being imitated everywhere. And via seamless integration with its Mobile Me online service (which got off to a horrible start, but is now working fine), Apple also rewrote the rules of how its device can work with the cloud.

In short, the smart phone market has changed dramatically in the wake of the iPhone. Here are some of the capabilities and features that I feel all smart phones must offer in order to be competitive with Apple's innovative device.

Phone. Obviously, but a smart phone must offer first-rate phone capabilities, including quick access to the phone functionality and contacts from the device's home screen. Contacts should be stored or at least mirrored in the cloud, as Microsoft is doing via My Phone for consumers and Exchange for business users.

Desktop-class and mobile web browsing. While many web sites are starting to offer mobile versions of their content, a mobile browser needs to handle the web in the same way that a desktop PC does. The iPhone does offer this functionality, sans Adobe Flash support, but Windows Mobile 6.5 only gets partway there with IE 6. The iPhone (and Android) also supports an amazing mobile web experience, including support for true mobile web applications.

Email. The iPhone is, perhaps, the most excellent email device I've ever used and Windows Mobile's Outlook-based Mail application is, perhaps, among the worst. (This is not so true for Exchange and Hotmail users, actually. But if you need to use third party IMAP-based mail services, Windows Mobile falls flat.)

Calendaring and PIM. A smart phone should be a first-class PDA and the calendar functionality should integrate with cloud-based services so that your schedule is never tied to just that one device.

Media playback. A smart phone should offer a first-rate multimedia experience and handle modern audio and video formats like Windows Media, H.264, and AAC. Here, Windows Mobile 6.5 falls far short--the Windows Media Player version in this system dates back to 2004, go figure. Microsoft could fix this problem immediately by integrating the excellent Zune software into its mobile OS. Smart phones should have normal headphone jacks that don't require adapters and should work with Stereo Bluetooth for wireless media access.

Camera and photos. Modern smart phones have high resolution cameras that support zoom, flash, and video. The iPhone only partially meets these needs, and then only on the very latest version of the hardware. Windows Mobile phones, by comparison, are all over the map, but the underlying software support is there. But they need to go further: The camera should support geo-tagging via an internal GPS and should integrate with online storage services like Flickr.

Messaging. Modern smart phones support both MMS and SMS and they do so fully.

App Store. Today's smart phones are backed by an online application store that is accessible both on the device and on the PC. Obviously, the iPhone innovated in this area to great effect, and now Microsoft has its own Windows Marketplace for Mobile. It's a good step in the right direction, and while I generally deride copying of any kind, it's necessary: Apps let users extend the capabilities of the device in new and exciting ways. This is now baseline functionality.

Tethering. When you are paying $80 and up each month for a smart phone, you should get tethering as part of the deal. This allows you to utilize the phone like a wireless modem (over USB cable or wirelessly), and get online with your laptop. This capability is determined and limited by the wireless carriers, but it is supported on Windows Mobile natively, which is the right way to do it.

Choice. Users should have a choice of device types that are built on a particular mobile platform. But that platform needs to be modern and not tied to a legacy past. The news is mixed for both iPhone and Windows Mobile here. The iPhone has no choice at all--you get one device, from Apple, in one form factor only, and it's only sold by one wireless carrier in the US--but the platform is modern and consistent. With Windows Mobile, you have a vast range of devices from every wireless carrier. Some have hardware keyboards, some don't. Some are clamshell devices. Some have tiny screens, but some have huge touchscreens. The issue, of course, is consistency. And Windows Mobile devices are almost too diverse: Finding an app that works properly on the one you have can be difficult.

Upgrading. A smart phone is a computer. That means you should be able to upgrade it to new versions of the software as they arrive. The iPhone does this. But Windows Mobile does not, at least not yet. I can tell you this: The infrastructure is in place to make it happen. And if Microsoft ever stops kowtowing to its wireless partners, it will make Windows Mobile a better system by letting its customers upgrade to new capabilities.

Online backup and remote wipe. If you lose your phone, it should only be a minor convenience because all of its contents are backed up to an online service--like Microsoft's My Phone--and you should be able to remotely wipe its contents so that others can't gain access to your private data. Windows Mobile does pretty well in this department. So does iPhone.

Moving on...

In the next part of this review, I'll provide some hands-on observations of Windows Mobile 6.5. I've got two and a half years of iPhone experience now, and this will guide my transition to Windows Mobile. While I realize Windows Mobile 6.5 won't best the iPhone--far from it, in fact--I am curious to see whether I can move to Windows Mobile without feeling regular pangs of regret. Is Windows Mobile good enough in its current 6.5 guise? I think it may be, possibly, but I'll find out for sure. And as soon as I can, I'll let you know what I discover.