When turning on my Clip I get the message, "Your subscription tracks have expired. Connect to PC to renew. I connect to PC, go Windows Media Center and sync my music. But the message continues to show up and clip won’t play all of the music listed.
An option this article doesn’t mention is to change the ripping format from .wma to .mp3. Then you don’t have to worry about the issue.
There are loads of open source programs out there that can convert audio files to mp3. Google will be your friend on this.