Apple didn't lose market share to MS, they lost it to IBM back when big iron was king and the closed architecture didn't help.
Actually that's not entirely true. When Apple screwed up the licensing of certain thing to MS, then lost it's court case with MS, that's when it really saw huge shifts in marketshare. Windows 3.x wasn't going to win anybody over. Once MS won the case, it was pretty much free to legally steal as much as it wanted from Apple's interface designs without having to worry about Apple anymore. Windows 95 came out and well that's when huge marketshare shifts came into play.
IBM was busy at this time with OS/2.
The biggest losses in Apple's world over the past several years have been in K-12 education. Part of it is political with IT directors making it impossible for Apple to even bid on contracts (like our local school district), and part of it is Dell who offers schools deals on equipment it had out on lease but has been refurbished. Tough to compete against that model.
Apple now has to win on it's own merits and the iPod is one of the few ways it has been able to have people look at the platform again.
To bring this back on topic a bit more, it's going to be hard for Apple to do some of the things that Creative and others are doing. Not because they don't want to do them, but they had to do some backflips for the record companies in order to get them to license their catalogs to Apple. This means there are some things you just wont see on an iPod, and you know maybe that's not such a bad thing. Maybe we need to stop trying to make these things vegimatics and use them for what they were designed for; that playback. In that area, I find the iPod very acceptable, I use it in the car and at work. In both places I'm not going to hear the difference between most of the units on the market.
Wayne