iTunes did not have a foothold in the marketplace until after the success of the iPod was evident.
As far as you "success of the ipod was evident" comment, that seems like solid case of hindsight on your part.
The iPod did not work on Windows (which was, what, 99% market-share in those days?) and required this insane thing called Firewire. Firewire. Even the name was funny to me.
I was a Linux fan-boy, patiently waiting for The Year Of The Linux Desktop, and was quite dismissive of that bulky little device, much like everyone else who was a techie. The Rio or whatever is what people were sporting.
And yet it basically destroyed the entire Taiwanese MP3 player market in the US in what, 2 years? Nokia should have seen it coming 7 years later...
Was?
iTunes is still the same trainwreck that it was 10 years ago.
Apple seems to work hard to keep it the same sluggish nightmare, no matter how fast the hardware becomes that it runs on.
I don't use it on Windows anymore - and I only installed it on there out of interest! Same went for Safari on Windows.
I use Floola to shove songs on my iPod. Might be worth a look? (Mine is a 6th-gen classic).
(Winamp was very popular on Windows, it had no UI guidelines whatsoever)
* While the first MacBook Air was crazy expensive and nearly universally panned for lack of a DVD-ROM drive, the MBA was repositioned in 2011 as the ultraportable replacement for the MacBook and is now the best-selling Mac.
* The first iPhone was blasted for its absurd price (due in part to lack of carrier subsidization), lack of 3G, lack of copy and paste (remember how upset people got about this? lol) and no third party apps. By the time the 3G rolled around, most of the software concerns were addressed and the price drop made sales jump $10m from 2007 to 2008.
* The first iPad (also known as the iTampon if you were following Twitter on the day it was announced) was criticized as being a giant iPhone, having a low pixel density (merely 1024x768), and lacking any ability to get "real work" done on it. Each iteration of the iPad has gotten more and more positive reviews due to the incremental changes (mostly in processor and pixel density) made over the years.
It more or less goes without saying, then, that I'm not really surprised that people expected more from the Apple Watch. Apple's really fortunate to have such a great community of rabid early adopters who are more than happy to put its products through the ringer and hold Apple to a higher standard.
"Failure" is not determined by "lots of complaints", but by "very few sales"
And as a counter-point, the Surface RT has a second generation and may have a third. Does this imply success, or that MS went "all in"?
http://en.m.wikipedia.org/wiki/File:Total_ipod_sales.svg
We know that it took off, but that was wholly on the back of iTunes - 0.99 tracks and much easier use than competitors sold the iPod, not some fundamental excellence of the device.
People forget now but while we revile iTunes generally now, at the time it was the killer feature of the iPod, and the initial iPhone success.