When working on a new playlist, I add every song I might want to use, including multiple songs by the same band, instrumentals I might use as the final track, and so on, and after I have 25 or more songs in there I think about selecting, sequencing, keeping it under 80 minutes, and including 50/50 men/women.
(I also am aggressively adding a Beatles song to every playlist until every great Beatles song that's never appeared on one of my playlists finally makes an appearance.) Every once in awhile, my working collection gets so big I decide to assemble more than one playlist at the same time (
see 93 & 94, 105, 106, & 107, and 111 & 112)
In the case of 223, I had 40 songs in the inbox already before I noticed I had ~35 guys and only 5 ladies. I then added 20 songs from women to get the ratio right. 60 songs means three playlists!
Sequencing three 20-song playlists with near-equal men and women, and no repeated bands, is too hard
for me to do off the top of my head. Sometimes I do my sequencing in IRL with little strips of paper - 83 and 208 are examples of this. For fun, I've included my final sequences strips of paper below.
