It really sums up nerds' lack of comprehension of the importance of user experience. It's like the UX version of the apocryphal "640k is all anyone will ever need."
The first iPod was terrible though and sold poorly. The 3G was the first good model, and they didn’t start taking off until the 4G. History only proves that his analysis was completely correct.
No, Windows support came with the 2G in 2002. iTunes for Windows wasn’t a thing and few Windows machines had FireWire, but the Windows-compatible iPod came out in 2002.
The 3G was the breakthrough model, but I lend that as much to the dock connector (which was available in USB and FireWire) and the growth of x-platform iTunes as anything.
The broader point that it required Windows support for the iPod to become mainstream is of course true. That said, the iPod was also the reason so many of us became Mac users in the early 00s because the “halo effect” was undeniable.
You're right. It really was the dock connector that made it a viable product for many people. The fact that the first iPods were Firewire (which I totally had forgotten about and I even had a 1G iPod) made it very difficult to make it work outside of the Apple ecosystem.