Windows XP pre-dates the iPod. Windows Media Player pre-dates the iPod by over ten years.
The whole post feels like you've re-imagined a lot of the history, certainly much of it doesn't align with my experiences and impressions at the time.
Meanwhile Apple had the monstrosity that was/is QuickTime.
The reason iPod was so popular was it's form factor/UI/UX/ease of use and the iTunes Music Store.
It also needed USB to become successful, FireWire held the iPod back from mainstream adoption.
If you bought your computer in a store -- like most people in the US at the time -- instead of building your own, it came bundled with some other product: WMP at least, possibly MusicMatch, RealJukebox (eventually merged back into RealPlayer), which you were likely using. Getting your Nomad or iRiver, a comparable devices to the iPod, to work with that, was not as smooth as the iTunes-iPod combo.
Nope, Apple had had iTunes since 2001, and by the time the iPod came out, I for one had ripped most of my CDs to iTunes and basically used the Mac as the primary music machine.
Even today, iTunes still depends on QuickTime, but given I haven't used Windows in almost ten years or seriously used iTunes in almost 8 years, I couldn't tell you whether that dependency is the old QuickTime 7 API or if Apple ported a subset of the newer QuickTime APIs over I also couldn't really tell you which they use on Macs* anymore either given I prefer to avoid launching iTunes whenever possible.
That said, iTunes up to about version 6 point whatever the last point update was, was genuinely a really great jukebox on Windows. It was easy to use, loaded fast, ran fast and I ran it nearly 24/7 on my old XP machine. iTunes 7 ruined all of that, and my first indication would have been when it took over an hour to complete the install process and the first run was dog slow.
* Apple did deprecate and remove QuickTime 7 from Mac OS X, that said, I wouldn't put it past them to maintain an API in maintenance mode exclusively for their own use, particularly when it comes to maintaining the many-heads of the beast that is iTunes.
I think the OP's point was that, while you could do this stuff on Windows, it wasn't nearly as functional, seamless, or simple as it was with an iPod and iTunes or even MusicMatch (which really, really sucked, at the time).
And the Creative Nomad ZEN Xtra with 60GB was phenomenal for a reasonably sized library.
For software, I recall two options:
MediaMonkey Gold, a media player that synced with ZEN players and could automatically convert media formats.
Notmad Explorer, a software suite from Red Chair Software that allowed for file and playlist management for the ZEN players.
Microsoft took about 5 years to catch up, no small part due to USB 2.0
XP was released on 25th octobre 2001. First ipod 2 days before, on 23th october 2001.
Clearly, the install base of these products significantly contributed to the software people used to manage their portable music players. In May 2003, a Nielsen report put Winamp's install base at 5.5 million, Windows Media Player at 43.1 million, RealNetworks at 26 million, and QuickTime at 13.5 million [4][5].
[1] http://www.nytimes.com/2000/01/10/business/technology-micros... [2] http://www.zdnet.com/article/apple-product-marketing-says-qu... [3] http://www.websiteoptimization.com/bw/0801/ [4] http://www.zdnet.com/article/music-players-market-share-wina... [5] https://www.cnet.com/news/aol-trumpets-new-winamp/