I found myself in similar situation. 800 + cd's ripped to apple loseless on my mac and a handfull of ipods, nano, mini, shuffle, video, etc. for different family members. I found an apple script that takes selected apple loseless tracks, rips them to AAC transfers the AAC to your Ipod, then deletes the AAC from your itunes library. Now there isn't a mixup of which files to toss and trouble keeping track of multiple trascks ripped to different compression ratios. here is the link.
http://www.dougscripts.com/itunes/scripts/scripts07.php
pete
http://www.dougscripts.com/itunes/scripts/scripts07.php
pete