Automatic iTunes Transcoding

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.

 

Do you know of any reason why this option can't be enabled for non-shuffle iPods? I used to have a shuffle but just the 60GB iPod now, so maybe thats why I haven't seen the option in a while. I can remember it took some time to transcode for the shuffle but I didn't really mind.

How do you keep everything up-to-date and in sync correctly?

 

Thanks tyr2, what you have setup seems like a good idea, however the lazy inside of me doesn't want to mess about with playlists.

If it's the best option going though, I'll take it, as it's better than nothing. I wish this was built-in to iTunes or someone came up with a plug-in or similar. I wish I had the technical knowledge to make it myself!

Ideally what I'd like would be to manage all my music on my iMac and the MacBook just nips in and syncs itself with the iMac (at the same time as converting it). No manual intervention at all. I can figure out how to sync files alright and I could probably get them transcoded but getting them into the library on the MacBook automatically would probably be hard for me to automate.