It must work more simply than this
I like My Sync, My Zune, and My Windows Media Player. I just wish they worked together better...
I wrote an article on the then new Zune, pointing out the disconnect in Microsoft's media strategy. Afterall, after announcing PlaysForSure, the then new Zune had no support for that format.
I have a nice Ford truck, one with excellent fuel mileage, comfort, towability, and total traction in snow. It even has Sync, the wonder box co-designed with Microsoft. I've enjoyed its many features, including the ability to play music files by attaching everything from a media player to a USB drive.
Except for playlists.
Neither the book nor the website explain how to merge playlists from either Win Media Player or the Zune software. Is this important? Who wants to hear disc 1/song 1 followed immediately by disc 2/song 1 from most 2 CD sets? Grrr!
Zune only generates playlists for the Zune. Win Media Player can show the USB drive, but good luck building and saving a playlist from and then to the USB drive. Sure, you can try altering track number in the song properties, but that won't work.
So you do what many are increasingly doing: find, install, and then use a piece of freeware and/or Open Source to do the stuff commercial software should do more easily. I picked up a nice M3U editor from cnet.com. Problem Solved.
I'm still enjoying my Zune, My Media Player, and My Sync. I just wish there was better integration among the common elements.