Apple sucks. Hard.
There are a number of ways to load an Ipod. You can use
Rockbox, my method of choice. This is entirely different firmware for the Ipod (man, I bet it just kills the stupids that I capitalize the I and not the p :laugh: ), which allows it to play flac and ogg-vorbis, among other formats, as well as be loaded just like the USB storage device that it is.
Alternatively you can use a standalone loader like
EphPod. Lastly, there is a plugin for foobar2000 called
foopod. And if you use winamp, I believe there's one for that too, but you're on your own as I don't recommend that player. foobar2000 > *.*