I hope Microsoft can do this.
It is frustrating that I cannot get my Media Player playlists onto my iPod. Also, some of my files cannot be read by iTunes, which is necessary to get the songs on the iPod.
See my post #8 on this thread. I believe the iTunes software that comes with your IPod will convert Media Player's WMA format to ITunes Mp4 format. It's been awhile but I've done it. To go the other way (from Mp4 to WMA) you need a software application like 'tunebite' to convert the files so they can be played by Media Player or burned to CD. This program must be purchased. I forget the cost. But it works.
I found that itunes was more than happy to convert all my files into its format, volunteer to be my default player, route me to the itunes store, and then tell me I can't play the stuff on any other machine (three hard drive failures later, I needed a special dispensation from apple to use the music I'd bought).