Stretch, thank you for your response.
I just tried playing this song on my iPod and it starts right away. Note also that it starts right away when I play it on my PC using iTunes and the file lives on the PC. (If I play it in iTunes on my PC, but use the firefly server to serve it up it doesn’t play at all.)
I have other files that were encoded by Nero (same workflow) and they play ok, so I suspect this is not yet the answer to this riddle.
What does the “offset” field in the server logs indicate? As I mentioned, the first serve serves to ipnumber:offset 0 while the second one (which I can hear) serves to ipnumber:offset 32. Perhaps there is a hint in that behavior.