iTunes/iPod Integration is Fantastic
After reading how several others (blogcritics.org, SuperDeluxo4.2, iPodhead.com) used Apple's iTunes Smart Playlists to get music onto their iPod, I began experimenting with how they work and how they let me use my iPod. I'm impressed.
In iTunes I've set up several Smart Playlists to select what music I want to hear. The "Daily Music" Smart Playlist, for example, selects any music not of the "Holiday" or "Comedy" genre, not rated one star, and not played within the past four weeks. When I sync with the iPod this playlist is copied to it.
After a song has been played it's removed from that playlist because it no longer meets the criteria: it's been played within the past four weeks. The next time I sync the iPod to iTunes those played songs are removed and new songs are copied to it.