Best way to send mail to a group of more than 500

One of our users has to send email to a group of more than 500 (all external, not spam). What is the best way ? At present the user is using a php script and while the emails are sitting in the queue to be sent, all other user's emails are queued. Is there any other way (not using a second server).
Also interested in knowing if there is anyway to see that these emails are not marked as junk by yahoo or hotmail.
Appreciate your help.

I would not have thought that 500 emails would take too much time to go out (but can the script be triggered at some time in the morning?). However, if you have a standard server then all outgoing mail will be getting scanned for junk & viruses (same as inbound) and that will take the majority of time spent. To avoid this, you can set up an alternative submission port which bypasses the scans. See UptimeJeff's web site how-to...
http://mac007.com/?Tips:AlternateSMTPPorts
The original forum thread prior to the website article...
http://discussions.apple.com/thread.jspa?messageID=3008740
As for yahoo/hotmail question, unless your server is badly configured (host name, etc) and/or the emails 'look' like spam, I would doubt they will trigger the usual tests. You could always create a yahoo/hotmail account to check.
-david

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