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I'm sure there was an issue with Postfix with loads of recipients (I'm sure the limitation I;m using has some reason to it :)). As far as I remember it treated the entire message as a whole, when it checked against timeout. On the other hand, every recipient triggers a delivery method you can find in 'master' config. So when you have some kind of converstion (Word2PS in my case) it happenend for every recipient separately. You can see it can be quite a while, when the file is large. The the timeout kicked in and the message got "redelivered". I think sending the mails individually should solve this problem if you can automate it.
OK so if I get this right, I have the limitation of the email server that may or may not be able to handle hundreds of recipients. I am using Postfix .. I guess I should look into it some more too.
I guess the most convenient way is to just send all the mails individually.
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