OK, so I have a smart play list that I call "Random LRP". Basically, it's like the party shuffle, except that it limits itself to songs that I haven't heard in the past two weeks. My library is large enough, that the list is always full at 100 songs.
So, just now, it cued up Stevie Ray Vaughn's Little Wing immediately after Jimi Hendrix' version of Little Wing. Now, if it had cued up Sting's version of the song, I'd have really thought that something was off. Even so, the odds of this happening are really slim.
But, that's the problem with probability. People do actually win the lottery despite the fact that playing it almost guarantees that you'll lose in the long run. So, no, I don't believe that there's anything cosmically "in tune" with iTunes' random algorithm. It's still random. It's just that randomness often provides interesting surprises.
Currently playing in iTunes: Little Wing by Stevie Ray Vaughan