Actually the bundle's not bad

It integrates with Windows, converts from just about anything to a format the Zen can play (even the MS-DVR files on my media-center box), quick to transfer, and has never crashed even after transfering a couple of thousand tracks to it. Once you have the drivers on your PC, you can also use mediaplayer 10+ to do the transfering as well (and if mediaplayer has embedded the cover images in your audio files, they'll show on screen when playing on the Zen as well).

Previous player was a Creative Zen Xtra, so I know of the pain you talk about, but this just does what it's supposed to.