Yesterday I took on teaching my friend Matthew from A Bollen Design about Drupal. We're helping with a project that, while there will only be a few users, seemed like a good fit for the platform. Normally my rule is that if you'll have a small team adding content then you should defer to a smaller CMS like WordPress, but this project will have a few more features just beyond what I think is reasonable for only WP plug-ins. It's not a tech project so I hesitate to think about custom development options.