I think it would be helpful to write the images and metadata for song tracks to the filesystem, rather than just the server cache. This way, a custom image for a song (CD Single artwork, etc..) would be permanently stored, much like movie posters and album art is now.
If the song is /Bad Company/10 From 6/Bad Company.mp3
Then write...
/Bad Company/10 From 6/Bad Company.jpg
/Bad Company/10 From 6/Bad Company.nfo