Heh. Actually, I figured it out, and even figured out a way to explain it clearly in the FAQ.
The only problem is that when I actually TRY it on my player it doesn't produce the desired results.
For instance, I know that there are a handful of tracks on my player that have a "plays" count of 20 or so. Everything else is in the 0-5 plays neighborhood. But when I create a "favorites" shuffle as the example, those tracks are not at the top of the shuffle when I hit it. They're not at the bottom of the shuffle when I wrap around backwards, either.
This counts even if I remove the "random" item from the list. In that case, I would assume I'd get a straight count-up or count-down by Plays. I don't. In fact, the resulting song list doesn't seem to be related to the plays count at all.