The iPod is what eventually got me back into the Mac fold. I purchased it in December 2001, even before it officially worked with Windows. I remember XPlay, Ephpod, and other "hacks" to get it to work with Windows. I even purchased a Firewire PCI card for my Windows XP desktop to get it to run. Of course, I managed to mess up the drive the first time, and took it to one of the brand new Apple stores 40 miles away, where the Genius Bar representative happily restored it.
I do remember the early criticism. In some respects, it was like the reaction to the iPhone 4S. Apple products in many ways fail to meet the hype but then greatly exceed the hype at the same time, if that makes any sense. People are "disappointed" that whatever they release didn't meet some wild speculation, but then realize that it's a great product. It happened with the iPod, the iPhone, the MacBook Air, and the iPad. All were roundly criticized by many "experts."