I've put some of my thoughts about the dynamics of the WMF-Community relationship into an essay on Meta, entitled "Why do They always get It wrong?"
I thought I'd share it here. Hope it's useful!
https://meta.wikimedia.org/wiki/User:The_Land/Why_do_They_always_do_It_wrong
(It's not specifically addressed at any of the current challenges the movement faces, though as it happens I first started thinking about writing this when I was making notes for conversations with various people explaining why I thought Arnnon Geshuri would need to resign).
Regards,
Chris