OK, to try to put some of these threads to rest:
1) Windows 98, 98SE, and ME are all dead products. You can no longer buy them.
2) Windows 9X (I'm going to include ME in this as well, because it's the same basis) is built on top of the old DOS. This limits it to 16-bit operation and 8 character filenames with 3 character extensions (this probably doesn't matter to you much, though).
3) Windows 2K/XP are built on what used to be called Windows NT. It's a much stabler base, supports a real level of security (patches aside; those are a different issue) and has a completely different architecture. Software written for 9X will run on 2K/XP, but only in a separate container that was designed for emulation. 2K/XP software
CANNOT run on 9X. Ever.
4) iTunes first came out in the tail end of the ME timeframe. ME had already been announced as a dying product with no further updates, and was ending service at that point. Apple made a decision not to attack this dying operating system and coded for 2K/XP, where things are far more similar to the rest of the world (NT was built on a Unix-style framework, much like OSX is).
This being said, it is
possible to use an iPod with 9X. There are a few products available. I believe both EphPod and Anapod work on 9X and will interface with an iPod. You will not be able to use the iTunes Music Store or the AAC format (unless someone gives you an AAC track, maybe). I don't work with either product personally, so I can't say anything about them, but you have options.
I'd
strongly recommend considering upgrading to XP, though...It generally a better OS than 9X.
