Patrick Daly has written a plugin called Email that allows site administrators to build custom text-based email templates to be delivered to users based on specific user activity. Based on the screenshots, this seems like it could potentially be a really useful plugin for delivering specific messages to users. You can download it on .org or peruse the code on Github. I definitely want to dive deeper into this one.
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This is very similar to our plugin: Better Notifications for WordPress
http://wordpress.org/plugins/bnfw/