So I was thinking the other day about my 20 Gb ipod and how it frustrates me that I can't put any lossless files on it because they take up way too much of my space. Then I was thinking how large my desktop drive is and how nice it would be to have all of my songs in lossless so I could really archive them instead of just having a low quality copy. So... What if you could have all of your files on your desktop in lossless and itunes would automatically convert your files to whatever format you want when transferring to your ipod. I know it would take forever to do everything, but once you get the first batch done, all you would have to convert would be the new things, 1 CD at a time. Quite reasonable I think. Best of both worlds! Maybe there is something out there like that and I just don't know about it, but I think it's a great idea and would make itunes the ultimate killer companion app for portable music players.