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Here's my take. Outlook first appeared in Office 97. Every newer version of Office through 2003 came with substantial improvements in Outlook - whereas the other modules were only facelifted in comparison. I haven't played with 07 yet, but I'd assume that Outlook has been improved again in some form.
From a security standpoint, your BEST bet is a 3rd party mail client that does not have a large market penetration - the hackers don't mess with finding security holes anywhere near as much as they do with stuff that's in widespread use.
I've been using Pegasus Mail for over 10 years - it's clunky and has a real hard time with HTML, but it's almost ironclad. It's also free. However, the developer has essentially quit, he needed to spend his time making a living. It also has issues with Vista that probably will not be fixed.
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