foobar2000... Well, I did until I switched to *nix. Now I use audacious because foobar in wine sounds not-so-great.

Why are there no good *nix media players? :(

As for the Zen stuff, if you're going to get one of the newer ones, note that they force you to use MTP, which is terrible. Creative's implementation of it sucks for transferring music, or at least it did when they released the MicroPhoto. I'm torn between hating all things Apple and hating MTP. I want UMS damnit. Also, Zen doesn't run RockBox as of yet, which makes me sad.