Steve, thanks for responding so fast.
All of the files I am attempting to put on the Shuffle (from MC and iTunes) are MP3s.
After trying it again on another computer I noticed that the playlist that is created on the Shuffle is always the name that you have given to the Ipod (i.e. MyIpod, IPOD, etc.) no matter what the name of the playlist is that you are syncing in iTunes. Tonight I also tried to copy a song from my library into the playlist on the Shuffle. When I do this, the song is copied over and from that point on will show up under ARTIST, ALBUM, and GENRE, but it never appears under the playlist. If I then close MC and re-open it, it still appears in ARTIST, ALBUM, and GENRE...so it apparently is writing to the main db on the Shuffle, but it is almost like it is corrupting the playlist db which stops the Shuffle from playing once it is un-docked.
One other thing that I have noticed is that if I copy a song to the Shuffle in MC, iTunes will crash everytime that I open it with the Shuffle plugged in, until I use the restore program to go back to the factory settings.
Thanks again,
Dan