I currently sync two playlists to my iPod. A "smart" playlist and a manual playlist named iPod Smart and iPod Manual respectively. The "smart" playlist is configured to select 115 songs ordered by date from my library where a: the rating is greater than two and b: the play count is less than two. The other serves as a way sync up a few current favorites or even a pod cast.
As the idea of an iPod large enough to hold your entire library goes the way of the virtually ignored "classic", I think apple would do well to make some improvements in the tools it provides for managing and syncing it's iPod devices. What are your tricks?
Update: as I was syncing my iPod this morning I realized you could limit a "smart" playlist by total bytes (in GB and MB). This is a far more reliable method for someone like me trying to use every bit on a small drive. I'm not sure if this is a new feature in iTunes 8 or if I just never noticed before.
