Extensions to publishing and more

For a client, I need to use WordPress more than optimally. Let me expand on what I really need:

Several web laymen will be using the site to publish stories, post photos and set dates to events. The site will display these stories just like posts. The photos will be done like Chris J. Davis once displayed his with Pages. The event calendar, however, is something I’d like to do from within WordPress. Are there plug-ins to this? Also, what plug-ins should I use to make WordPress easier for the average Office Word user? Any other suggestions to make it more of a normal site to the user? (How is photo uploading?)

Your input would be appreciated.