I think it's more how they are tagged than just the filename, that makes a difference.
I use this format:
Song Number - Artist - Song Name.mp3
(02 - Van Halen - Dreams.mp3)
If there is more than one artist, I tag (id3) it on the song title like this:
Artist - Van Halen
Title - Dreams f/the Other Artist
But the filename is still the same.
I did it this way for better support with my iPod. Rather than have a different entry for each artist and the artist/featuring, I just made all songs by the album's artist. In RR, the tags are usually read rather than the filename.



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