And that, my friends, is the reason I stick with iPod. The iPod integrates beautifully, seamlessly and effortlessly with my iBook.

To answer the original question, unfortunately if you delete songs from iTunes, next time the iPod syncs, it too deletes the same songs. Unless you manually sync which is rather tedious and breaks the tight integration between iTunes and iPod.

I have scoured the Net looking for a better solution but my efforts have so far been futile. So my temporary solution is to free up my iBook's hard drive by backing up infrequently played albums in my iTunes library to CD in mp3 format. You can back up several albums to 1 CD.