Is it time to ditch Windows Mobile?

For all the talk there's been about Microsoft's big Vista problem, much less has been made of its smaller operating system, Windows Mobile, which has some major problems of its own. Truth be told, I'm a longtime Windows Mobile user and I have to say it's been a frustrating ride. There are things I really like about the OS--and things I find really irritating. However, the frustration stems from the fact that every time I think it's really going to turn a corner, Windows Mobile continues to disappoint. And I'm seriously considering giving up on it.

Take my current situation. I own a Sprint Mogul. Like with all cell phones--and smartphones for that matter--I was smitten with it when I first got it. It was a nice upgrade over the PPC-6700--not only in terms of design, but it performed better all around. Alas, with time, it's experienced its share of problems, even with a couple of firmware upgrades that gave it faster data speeds from Sprint's newest 3G network (Rev A), added GPS, and fixed a few bugs. I need a new battery, the keyboard doesn't work as well as it used to, the phone freezes a fair amount, and when I touch icons or open fields on the touch screen, it often takes a few taps to get the reaction I want. (Some people refer to this as the Windows Mobile "delay" syndrome).

I've been tempted to migrate to the Mogul's successor, the HTC Touch Pro, but I'd be looking at spending about $300 on that new model with a couple of rebates thrown in, one of which is of the mail-in variety (I hate those). Of course, to get those discounts I'd have to sign a new two-year contract, which wouldn't be the worst thing in the world if I didn't know that by the time my contract was up--in June--Sprint would be offering the Palm Pre, AT&T would probably have a new rev of the iPhone, and at least one (if not more) new Google Android phone should be available. I also like the looks of Nokia's N97. Why should I use up my potential discounts when the offerings will be look better a few months from now?

Even though it isn't saying it, I think Microsoft knows it's got a challenging situation brewing--which is why you're starting to hear the company talk a lot more about Widows Mobile. In the middle of February, to bridge the gap between version 6.1 and 7.0 of the OS, we'll see 6.5, and Microsoft execs are starting to allude to new features and fresh starts. Meanwhile, of course, Google, Apple, Blackberry, and Nokia (Symbian) will continue to upgrade their mobile operating systems.

The biggest problem for Windows Mobile has always been that it's bloated and runs too slowly. It's just a beat or two (well, maybe more) behind the iPhone OS in terms of zippiness and it probably doesn't help that HTC throws its own carrier-centric, custom user interface on top of the OS. The integration of multimedia applications has been woeful: the mobile version of Windows Media (which includes video and music playback) is simply pathetic and neither the Touch Pro or Mogul have standard headphone jacks. True, Windows Mobile has always been more geared to business and corporate professionals, but now that the iPhone offers Microsoft Exchange support, more of those types are migrating to the Apple camp.

On the plus side, the Mogul and Touch Pro have some things in their favor. Both models have memory card slots (you can swap cards in and out), removable batteries, and most importantly for me, they can be used as wireless modems for your laptop via a Bluetooth or USB connection. The voice-based turn-by-turn GPS on the Touch Pro is nice (so long as you can get a Sprint PCS connection) and the Mogul and Touch Pro shoot video and have stereo Bluetooth--features currently missing on the iPhone. I also prefer a physical keyboard to the iPhone's virtual keyboard. And finally, Sprint's all-you-can-eat data plan is significantly less expensive than AT&T's iPhone data plan. Much has been made about the cost of ownership of the iPhone compared with other phones, and there's no doubt I'd be saving money in the long run with a Sprint smartphone, whatever it is.

I'm trying to hang on, but it's tough. It's the little stuff that bugs me. For instance, it took four tries to sync the phone with my desktop PC (using the Mobile connectivity software built into Vista) and the integration between PC and phone is still archaic and lame compared to what you get with the iPhone. While it's nice that you can run multiple applications at the same time on a Windows Mobile device, the OS still doesn't seem to manage its resources well and gets bogged down. (I'm always closing out applications that keep running unnecessarily in the background.) Software/firmware upgrades are few and far between and I lost any desire to add new software packages to the phone because it was hard to find them and they cost too much. I envy all the free and cheap applications you can download to the iPhone from Apple's much-lauded App Store. It also hurts when your 70-year-old father taunts you with his new iPhone, saying how great it is. (No parent should achieve tech superiority--not in my family anyway.)

Microsoft is vowing to fix a lot of the things that irk me. The multimedia features will certainly be improved and a rumored app store, SkyMarket, is in the works along with Xbox 360 and Zune integration. In a recent article by CNET's Ina Fried, Andy Lees, the Senior Vice President of Microsoft's Mobile Communication Business unit, says some interesting things about the future of Windows Mobile, the mistakes the company has made, and how a new strategy implemented a year ago will pay dividends over the next 18 months. Lees talks about how next year's phones will be incredibly powerful, feature "dual-core processors, super-fast data connections, and graphics power rivaling that of the original Xbox."

On paper, at least, that all sounds exciting. But I have a feeling that Windows Mobile 6.5 will be just another tiny incremental improvement that just won't cut it. Can I hold out for Windows Mobile 7? If it turns up in June, maybe. If not, it's probably sayonara--or, as they say in Redmond, goodbye.

As always, feel free to comment. Will the iPhone, Android, and Palm Pre bury Windows Mobile? Or will Microsoft deliver on its promise to build a superior mobile OS?

Disclaimer: I was able to play around with a review sample of the HTC Touch Pro, but Sprint was unable to temporarily transfer my Sprint number over to the phone so I could use it on a day-to-day basis for a few weeks and really get to know it. So my observations of the phone are somewhat superficial. Feel free to tell me what you think of the phone if you own it.