Although this doesn't help you fix Outlook in this case, I recommend using Mail Chimp for this type of thing. It allows you to maintain your lists, provide opt-in and opt-out functionality, it authenticates your outgoing mail (so you don't get snagged by filters as much). It is all web-based so it doesn't bog down your own resources. You can develop templates, pick segments of your list to target, etc. And... perhaps best of all, it cleans your lists automatically based on your bounces.
At work, we used to go through the same thing trying to send out our legitimate newsletters. Sending out smaller batches, running our own mail server, etc. Nothing has really worked as well.
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