I'll go out on a limb and make a guess that you are using the Postfix that shipped with OS X? The reason I say this is that I noticed the exact behavior you describe with the default Postfix on Panther. Mail would often sit there in the queue until a subsequent message was sent, and then all would be delivered, as if the new message woke the queue up or something. Very strange.
Bing bing bing. In fact, I'm using the Postfix/Cyrus install that comes with Panther Server. While I'm glad they moved away from the horrid system they were using before, they apparently were still able to mess some stuff up. I'll play with it and see if I can make it be nice.
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