Automator, iTunes won't shuffle first song

I have a remote computer running iTunes playing a shuffled playlist. I wrote an Automator task to reshuffle the playlist and start it over again. The Workflow is simple:
Get Specified iTunes Items (for a playlist with one blank song)
Play iTunes Playlist
Get Specified iTunes Items (with the desired playlist)
Play iTunes Playlist (with Shuffle)
I found that I need to play another playlist in order for the desired playlist to be reshuffled. Otherwise, it picks up where it left off. So the first half of the workflow does that.
Here's the curious thing, the playlist gets shuffled for all but the first song which is always the same! If I do it manually in iTunes, it shuffles fine. Using automator, the first song stays the same no matter how many times I run the shuffle automator.
If I restart iTunes or even if I play a few other playlists manually, it shuffles once, then has the same first song problem for the subsequent runs.
Any ideas?

Is it a smart playlist?
If it is, you could try:
http://dougscripts.com/itunes/scripts/ss.php?sp=reshufflesmart
Or you could just set that playlist as a "source" in party shuffle. And just have automator play iTunes Playlist "Party Shuffle".

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