Re: Windows lossless & iPods
iPods do not support WMA files. Only MP3, AAC, m4a, aiff, WAV, Audible.
I believe that through Windows iTunes you can do a batch convert of the WMA files to the ALAC format (m4a).
If you want lossless on your iPod I would recommend m4a if you can get it to work, or AIFF. WAV as a third option.
Sorry, but Windows doesn't play nice with the iPod. You can always go for a Creative Zen, Rio, or something. Especially if you are using just a PC and want the WMA support.