SOFTWARE
ITunes Opens New Front on Beleaguered PDAs

Handheld computers have been in a pitched battle to defend their turf from new breeds of mobile phones that have been relentlessly poaching palmtop functionality. Now handheld makers have to face a new threat -- a rear guard action from Apple Computer (Nasdaq: AAPL) and its indomitable iPod.

Apple recently raised the curtain on a new version of its free music management software for Windows, iTunes 5, and buried among the application's new bells and whistles for searching, shuffling and organizing songs is -- lo and behold -- a feature for synchronizing contacts and calendar items from Microsoft (Nasdaq: MSFT) Outlook programs.

Easy Setup

Setting up the sync from iTunes is, as one would expect from Apple, very easy.

You connect an iPod to your computer. Then you navigate to iPod preferences in iTunes. Check a few boxes.

The next time you sync your iPod with iTunes, your contacts from Outlook or Outlook Express and calendar entries from Outlook will be sent to the music player. Subsequent synchronizations will keep your contacts and calendar up to date with changes made to your desktop application.

Onerous Navigation

On the iPod, you access your contacts and calendar as you would your tunes. That can be a bit onerous for locating contacts because, without a search function, it can lead to endless scrolling -- especially if you have more 3500 names in your contact folder as I do.

You can filter the contacts you send to the iPod by group or mailing list. That gives you an opportunity to create a more manageable subset of your contacts on the music player. But more flexibility is needed here. On-iPod filtering based on contact categories -- as is done by Palm Computing's operating system -- would be a welcome addition.

The calendar feature worked well, even on my first generation iPod with a two-inch monochrome screen. When you access the calendar, a monthly grid appears. Days with appointments or events are marked by a dot. When you select one of those days, a daily calendar view appears on the screen.

The new iTunes contact and calendar features in their current form don't pose much of a threat to full-featured handheld computers like those made by Palm, Compaq and HP (NYSE: HPQ), but they do open another front that must be carefully monitored by handheld makers lest they be caught in a pincers, with mobile phones on one flank and digital music players on the other.

Evolutionary Changes

Other than the new sync feature, changes in the new iTunes are more evolutionary than revolutionary.

There's a new search bar that permits more granular ferreting of iPod material. After performing a keyword search, it can be refined, at the click of a button, by category--music, audio book, podcasts, video or booklet. Music hits can be further filtered by artist, album, composer and song.

Apple's also tweaked the program's shuffle feature. "Smart shuffle" reduces the probability that a song by the same artist or from the same album will play consecutively.

Parental Controls

Parents can impose controls on iTunes to prevent their children from accessing podcasts, shared music, the iTunes music store or tracks at the store with explicit lyrics.

A long overdue improvement is the ability to create folders in the Source window. That window displays various sources of music and playlists created with the program. In the past, as you created more and more playlists, the display became more and more unwieldy. With the new folder feature, you can devise a nested folder structure as you would on a computer hard drive for easier navigation.

You can also save the lyrics to songs with the new iTunes. That requires entering them into the program by hand, or at least some cutting and pasting, a tedious task at best. Now if the program found and imported the lyrics automatically into itself, that might be something to get excited about.