Glad you were able to reproduce. Tried properties on the playlist, didn't' help. You can see it fire the task to do the work but nothing changes. Now that I've tried this, I'm not sure its what I want though.

I was thinking that all the videos with a certain keyword would be in a subfolder of the playlist. But it seems that in that subfolder, each video has it's own folder and you have to go into it to play it. Too much drilling.