First off, I add a song or two about every two days, and second, I am not worried about the display in emplode in the columns. It's the way that the songs end up when you upload them to the Rio. Basically when you first create a playlist everying you put on there in the first sync will be in alpha order (at least that's how mine did it), but when you add some new songs to that same folder the next day they start to organize by order that you put them on the rio. In emplode you can sort the lists anyway you want, but there's some extra steps to actually change the sort order on the Rio. And I have to change the sort order for each artist's playlist everytime I add a song.
This probably seems more complicated than it is. I'd almost have to show you in person I think. Oh well... maybe the soup views system will help me. I hope they are in fact working on that right now.