How do I create a smaller (iPod-sized) copy of library?

I’d like to create a much smaller copy of my iTunes library, one that will fit on my iPod. I’ve been using Apple Lossless encoding for all my CD ripping to maintain high sound fidelity, but it’s now over 100GB and growing.
Is there a way to create a copy of the library with lower audio resolution (like AAC or even mp3) that maintains album artwork, playlists, ID3 tags and the like?
Thank you.
Oops. This should have gone in the Importing & Burning subcategory!
Message was edited by: BflatBlues

There are several ways to go about this.
Assuming plenty of hard drive space for the moment, one way is to set your import preference to something like MP3 or AAC in order to do the next steps. Now select all the tunes in your library you want to put on the iPod in a smaller format. Right click on the bunch and pick "Convert to XXX" where XXX will be your import preference, which we just changes to MP3 or AAC. Pick that and iTunes will then convert all the selected tunes to MP3 or AAC and place COPIES of them in your library (the original Apple Lossless versions are not touched).
Then you could create a playlist where the rule was to include "Kind" is MP3/AAC. Then set up your iPod to only sync that playlist (rather than the whole library) and you will end up with only MP3 and AAC files on your iPod.
Of course your library now has two versions of all the songs you converted.
If you wanted them in their own library, you could start a different library, add those converted versions to the new library and then remove them from the old library, but now you have to maintain two libraries. With the above method, you only have to maintain a single library.
In iTunes you can also right click on any header, get the pull down of all available headers you can show and pick KIND (which shows what format the tunes are in). You can sort on this column if you ever want to group together all the MP3 or AAC files to be able to select them all at once and to do group things on them like deleting them all, dragging them to a manually created playlist or onto a manually updated iPod, check or uncheck the box in front of each one, etc.
Patrick

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