Just an update, to help people who might want to do the same thing: If you have iTunes on a Windows machine with Windows Media 9 or better installed, iTunes will automatically convert any (?) .wma files you drag into the library, and you can put them on the iPod from there.
I'm running a Mac, so I used Virtual PC with Windows 2000, set the iTunes music library to point to my VPC shared folder on the Mac side, and let it take it from there. I had it convert them to .aac format files to keep them small, and Mac iTunes is of course happy with these.
Why can't you do it on just a Mac? Because Microsoft only makes a bare-bones v9 player for the Mac, and iTunes has no way of accessing those files without the full Windows Media support that's missing. Such is life. But convoluted as it is, this system works and I'm happy!
Pres
I'm running a Mac, so I used Virtual PC with Windows 2000, set the iTunes music library to point to my VPC shared folder on the Mac side, and let it take it from there. I had it convert them to .aac format files to keep them small, and Mac iTunes is of course happy with these.
Why can't you do it on just a Mac? Because Microsoft only makes a bare-bones v9 player for the Mac, and iTunes has no way of accessing those files without the full Windows Media support that's missing. Such is life. But convoluted as it is, this system works and I'm happy!

Pres