I gave up my iPod nano to my wife, as her shuffle was dying. Now I am trying to use Canola to replace it but I find myself lacking a simple sync of a random (and size-limited) playlist from my music library...

I was trying to figure out how to do this from iTunes or desktop Linux as I have these available. I saw the iTunes + Automator thread but I don't have a Mac with Tiger & automator on it.

I was thinking along the line of generating a podcast based on a smart playlist, then using gPodder or something to download it. But I don't know if anyone has done this already? Is there any other way?

Thanks.