I guess I'm a tad OCD when it comes to sorting my playlists. I have them set by year, with songs within often grouped by their genres, though more often it's by how well they sequence from one to other. A mellow funk song easily trails into a noodling jazz-funk piece, but sometimes, a hard rock song ends with a protracted cymbal ring that perfectly meshes with the first ten seconds of an ambient song. And that song then fades out, that in turn is followed by a fade-in pop soul song.
Anyhow, my year-by-year playlists (currently from 1956 up to 1974) range from 400 to 1100 songs, with something of a 90% perfect smooth sequencing. The playlists also really long, in the range of 18 to 80 hours. Each day I find at least one new song to add to these playlists. To facilitate and retain cohesion and a pleasing listening experience, I have a created an expansive document that labels each song with their respective genre and position in the playlist. That way, I don't have to rely on guesswork when it comes to finding a good spot for a new song.
Yeah, this is pretty OCD. And kind of satisfying, too.
TC's playlists still make mine look small, so, um... Yay?
Sigs are rather pointless, except if it's to showcase animation and images.