One thing not discussed which I think is important is the history of the WP community, it gives context to how it's evolving. In my opinion the direction of WP has always been very self-centric, but now we see protectionism taking over from innovation. This is due to the commercial viability of WP, WordCamps, and people having a financial stake in using WP.

It has become territorial in some regards and to be frank not very interesting. The attraction now is based heavily on finance, when you look at the innovations happening in the industry (news blogs for one example) WP is not even a discussion point.

The challenge is the barrier to entry is so very low, to combat this WP needs to really bring some innovation to the table and along with it a more diverse user-base will follow, unless they hire Steve Ballmer..