Great post and great topic.

I believe there is one critical point that you touched on gently but missed when it comes to WordPress. "Know Your Userbase" is a very tricky notion, especially with a diverse user base such as the WordPress userbase.

However, beyond the diversity, I believe there is one user group which is most neglected in the WordPress community. For the sake of simplicity (and for now having to call them the most neglected in the WordPress community) Non-bloggers. I believe this is a huge majority group that includes people such as:
- New users.
- Users with low computer literacy (may have a blog but refrain from using it because they can't get over the learning curve).
- Users who prefer simplicity and go to something like Tumblr.

With Non-bloggers you can't really get to "know them" - they are a silent voice. You couldn't get much out of them even if you could reach out to them. Yet I believe that failing to address Non-bloggers is a compromise on WordPress' core mission to democratize publishing. I am under the impression that a core democratic feature is giving everyone (that wants it) a voice. WordPress comes up short as it gives a voice only to those who can figure it out. Unfortunately the deeper you delve into the WordPress community - and as your approach development circles the less interested they are in doing anything about this since they love WordPress as is (with all of its options and features).

With this in mind I believe there is another critical group of WordPress users which are not even considered part of the WordPress community. This is people who have a commenting account at IntenseDebate. Though they may not consider themselves bloggers, they essentially are - their "blog" is distributed across the websites where they leave comments. Automattic is in a unique position to make build make a bridge between commenting and blogging because they do both (Disqus can't do this because they only do commenting). Ultimately every IntenseDebate account has the potential to mature into a self-owned web-presence - a blog!

Both of this groups are systemically alienated by the underlying qualities of the "knowing your userbase" approach. You need to design for them rather then study them ... but as Matt himself acknowledges (http://gihyo.jp/dev/serial/01/software_designers/0033) WordPress is not (yet!?) good at doing this.