The newest version of winamp has me thinking.
The newest Winamp contains an implementation of MusicMix software, it automatically analyzes the acoustics of your audio files and creates a categorized database. You can then select any song in your library and click a "mix" button and it will create a 20 song playlist filled with songs similar to the song you selected.
Now, I'm assuming it would most likely be illegal to write a program to read the database that winamp creates, but would it be possible to write a program that would analyze the acoustics of your tracks, and store the database on the iRiver. Then, have an option to "Mix" a track and have it look up similar tracks in the database to create a playlist?
I'm not entirely sure how difficult this would be to do...I have no programming skills unfortunately. What I'm doing now is mixing tracks in winamp and just copying the playlist over, but sometimes you just want to hear songs like one song that you didn't plan for earlier.
So, possible reality or far fetched idea?