I've had my Hero for a day now, and I haven't encountered this issue.
There might be two separate problems:
1) The Hero isn't detecting any more whether headphones are plugged in or not because the background application that is responsible for this is no longer responding - I'm pretty sure that a hard reset would have fixed that.
2) The Hero can't detect that headphones are being plugged in, because the detection mechanism inside the phone is bust ...
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