Shuffle no longer working with headset

Today I got prompted to upgrade my iPod software so I did...and the shuffle (2nd gen) no longer works. The flashy lights were green orange green orange. I went to the help website and dutifully restored factory settings with iTunes. Still doesn't work. Played with various permutations of the off switch (including the 5 second wait mentioned on the help site)and repeating the restore pathway and that didn't work either. The shuffle loads music fine and iTunes recognizes it and even plays the music but when I undock it (making sure to disconnect the shuffle properly) and connect headphones and hit play, the green/orange blinkies reappear.
Any ideas?
itune version is 7.3.1.3
ipod version is 1.0.4
I suspect this may be part of the problem. I can't upgrade to the latest version of iTunes because of my OS (win 2000). So I'm hypothesizing that when the shuffle tried to update, it failed due to the old iTunes version and somehow the drivers got screwed up.
Also, I just downloaded the iPod reset utility and tried that to no avail.
Any ideas? or should I just go to a store?

It's not a hardware issue. I have the exact same circumstance. After being prompted and then updating the software on my shuffle, it quit working. All I get is the green-orange flashing light. iTunes recognizes it's connected, restore works, and syncing works, but the shuffle does not work.

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