I could have sworn iTunes had an option to automatically transcode files to a certain bit rate when syncing with an iPod. It wasn't via some weird plug-in, it was a proper option in the iTunes preferences pages. I haven't seen this option for a very long time and I'm not sure if its been removed or not. Am I insane or was this once a feature? It would be so handy as I have my Lossless Library (300GB so far) on my iMac and would like to have a lossy version on my MacBook.