In April 2000, Microsoft and its partners released the Pocket PC, a handheld device based on Windows CE 3.0 that Microsoft designed to compete with market-leader Palm OS. At the time, it didn't seem to stand a chance because users had already ignored all the previous products based on Microsoft's componentized OS for small devices. But despite high prices and an unclear future, the Pocket PC took off, especially Compaq's gorgeous iPaq. Today, the Pocket PC is a force as the Palm OS continues to lose market share. It reminds me of the early days of the Internet Explorer (IE)/Netscape battle, although the outcome in the handheld PC market is less certain.

In any event, I wasn't what you'd call a fan of these devices. I tried just about every handheld device ever made, including the recently discontinued REX, various Palm OS-based devices, Microsoft's earlier Handheld PC and Palm PCs, and the Pocket PC—and I just didn't get it. I saw people on the train or bus, tapping away at those little screens, and wondered what they were doing. And when a friend of mine picked up an iPaq last summer, I bet him that it would be only a matter of weeks before the device started gathering dust on his desk. I figured I'd buy it from him at half price before long.

That never happened, and a series of events led me to purchase a Pocket PC of my own. One reason I made the purchase was that I was writing a book about Windows XP digital media (Great Digital Media with Windows XP, available soon) and needed to write a chapter about portable-device integration. But a second and more important reason was that I travel a lot, and I found that accessing my laptop on the road to look up appointments was time consuming and clumsy. I needed a better solution.

I bought a Hewlett-Packard (HP) Jornada 525—an inexpensive model, which in the Pocket PC world means I spent $350 instead of the usual $500. The Jornada features Pocket versions of Microsoft Office applications, and you can integrate the device with your Outlook-based tasks, calendar, inbox, and contacts, which is how I used it, at least at first. And because the device is instant-on, your information is only a stylus click away.

But another Pocket PC feature makes it unique—a version of Windows Media Player (WMP) that can play MP3 and Windows Media Audio? (WMA) audio files and Windows Media Video (WMV) videos. And if you have a headset, it can do so in full stereo sound. I found this feature intriguing, but almost useless at first, because the Jornada I bought included only 16MB of RAM, and even the most powerful Pocket PCs ship with only 32MB or 64MB of RAM. Because you have to divide up this RAM between your OS, applications, and other data, you don't have much room left for digital media files, even with the handy transcoding feature in Windows Media Player XP (WMPXP) that lets you shrink audio files as you copy them.

The Pocket PC's promise is expansion. The HP Jornada and certain models of the Casio Cassiopeia feature industry-standard CompactFlash (CF) expansion, and you can add CF capabilities to an iPaq with a slide-on sleeve. Previously, the largest CF cards I owned were 32MB modules, which I generally use with my digital camera. But I decided I could dramatically expand the Pocket PC's possibilities if I could get a CF card with higher capacity.

In the end, I purchased a 256MB Viking CF card for only $129 and a 128MB Memorex CF on sale for about $80. These cards let me stock up on music and even movies, which I can listen to or watch on plane flights. The device and CF cards also let me fly lighter, because I don't need to bring a dedicated portable audio device. I even use the Pocket PC as a music player while I work out on the treadmill.

Pocket PCs and CF cards are starting to come down in price, so if you're looking at such a device or at CF expansion, I recommend you shop around. If I had to do it over again, I probably would have purchased the market-leading iPaq because it's the best seller, and it seems to have more add-ons than any other device. But Toshiba will soon release a nice Pocket PC that features both a CF slot and an SDRAM slot for double the expansion, which should raise the bar for the other players and lower prices across the board.

It's now possible to take a sizable music collection with you in a package that fits in your pocket. And that device is much more capable than a standard portable audio device. It's definitely worth looking into.