My iTunes library is much larger than the capacity of a 4GB (or even 8GB) Flash-memory-based iPod. Therefore I searched for a solution that would allow me to automatically copy a selection of songs I'm actually listening to over to my iPod. I didn't want to bother changing the playlist I am syncing with the iPod manually every week or so.
The solution was based on this AppleScript snippet I found on the Internet, with some changes to make it work the way I wanted it to work. The script adds albums to a playlist based on the songs I recently played. In that way, the iPod is always filled with the music I'm enjoying right now.
2br
Here is the script:
Mac OS X Hints
http://hints.macworld.com/article.php?story=20080922151542821