I've got about 800 songs on my Nano, and constantly use the Shuffle feature when playing. Has anyone noticed that the random factor when doing this isn't so.. uh.. random? It really seems like I'm hearing the same 50 songs over and over.
When the Nano is connected to iTunes, you can see how frequently songs have been played. I was amazed that some have been heard 20 or more times in the past few weeks, where many others have never been played! The deck is definitely stacked..