I can relate to the random sequence "challenge" of iTunes (etc.) discussed in the NYT article. Here's an example of how I've overcome the challenge: I have a Playlist called "Quiet Jazz." Most of the songs are either female or male vocals with a smattering of instrumentals. Using the random feature, iTunes will play several female vocals in a row, for instance, which I don't like. My solution was to use Comments to enter a play sequence number -- 01 to XX -- for each song, after I edited the Playlist to a play sequence of something like female vocalist/male vocalist/instrumental. I order the songs within this Playlist by sequence number (Comments). This is similar to radio-station programming. It's more time-consuming up front, but it avoids funky stuff caused by the random feature. I realize this approach is also static, but I get around, to some extent, by using a different starting song each time I start the Playlist.