I've been thinking about this a lot lately. I've been working on WordPress projects that put an emphasis on narrative storytelling with multiple authors. One experiment being family websites that allow a whole family to tell their family history in compelling long-form fashion, while writing new chapters via ongoing blogging/journaling in areas that they are interested in.

By far the biggest challenge so far has not been setting the sites up or achieving the functionality I need, but making WordPress approachable for the whole family. Anyone my parent's age, or older, are incredibly intimidated by the whole process and it's been next to impossible to gently on-board them.