I have a web application running on Windows IIS. This app has a database where each item has a unique key (1, 2, 3...), and a list of email addresses (among other things).>
Event Sinks aren't difficult at all! In fact, there are about a dozen examples written in VBS (which runs on a Win server using WSH) which accomplish exactly what you wish to do. The OnArrival event sink runs in REAL-TIME using any computer user account you wish w/o any security risk since the message is asynchronous and doesn't report back.
This is actually a terribly easy thing to do - one of the easiest. Once set up, it never breaks either. On one server I've had one running for more than 9 years processing a few thousand incoming messages per day! I've set up about a dozen of these things - if it takes you more than a couple hours, you're doing it very wrong. If it were any easier than this on UNIX, my grandmother could be a UNIX programmer so I wouldn't go bragging that this is easier to do on a UNIX server.
http://msdn.microsoft.com/en-us/library/ms528023.aspx
http://support.microsoft.com/kb/894286
http://msdn.microsoft.com/en-us/library/ms526206.aspx
http://msdn.microsoft.com/en-us/library/ms526620.aspx