This insight hit me once again when I tried to install iTunes 5.0.1 (purportedly offering "several stability improvements over the original 5.0") on one of my Windows systems. When I rebooted--or attempted to--I discovered that it had rendered the PC effectively inoperative.

Every time I pressed the power button, the PC would display the Windows boot screen and then go into a dead hang. The thing wouldn't even boot via the <F8> key and Safe Mode. What saved me was the "Last Known Good Configuration" option--once I actually read the screen and figured out that in a typical bit of stupid Microsoft interface design you have to press the L key to make it work.

After the system's resurrection, iTunes reported that it was still trying to install itself, a process I nipped in the bud with brief trips to Task Manager and Add/Remove Programs. A unique case? Nope. I found similar tales of woe on the Web. And then I remembered the time I bought a friend's daughter a $100 iTunes gift certificate to go with her bat mitzvah iPod.

It worked for one entire song. Then iTunes deducted $20 for two albums, but in lieu of tunes delivered two messages declaring that "an unknown error occurred." Since there was no phone number available for Mom to give Jobs's Tune Town a piece of her mind, she used online customer service--and never heard back. The problem, which arose in June 2004, did not get any response until August, and the matter was finally resolved in September thanks only to my complaints to Apple PR folks. Will I ever buy music from Mr. Jobs again? Guess.

There may be something about music services that does not love PCs. When I installed a version of Napster on a different machine a few months ago, it crashed even harder--and, as I discovered when Chkdsk revealed dozens of cross-linked and otherwise munged-up system files, crashed irrevocably. That episode required a complete refurbishment of the hard drive from the restoration discs.

These incidents are hardly the only ones where digital media products don't work the way they should. I like the idea of Windows Media-based subscription music plans like Napster's and Yahoo's, but I hear enough horror stories to keep me listening to radio and buying CDs. And though Windows Media Center PC proponents always talk a good game, every Media Center I've tried has had serious failings. Devices for streaming entertainment over wireless networks add layers of complexity and awkwardness.

Decentralization isn't always a bad idea, either. If a CD goes bad--and I can't remember the last one that did--you're out a few bucks. When your hard drive with hundreds of songs on it goes bad, you may be out many hours of your precious time fixing the problem.

Add in the fact that most PC-based collections degrade the original's sound quality at least a bit, and it turns out that keeping all your music on a computer makes the most sense if you get your collection for free by stealing it--exactly what the iPod's packaging smirkily advises against. I don't steal. So for me, for now, I'll continue to store my music library in a cabinet that software can't break.

Contributing Editor Stephen Manes is cohost of PC World's Digital Duo, on public television. Click here for more Full Disclosure columns.