I love WordPress and have chosen to use it as my primary client CMS.
One frustration I have and wanted to chime in on is... changes to existing features. Having a software background, I understand your challenges with product evolution and updates.
The problem is that WordPress is being utilized by a wide range of people. The fact that it can be used by that wide spectrum contributes to its success.
When features are changed or removed, people who can wear the programmers hat aren't significantly impacted. They're disrupted but it's usually a relatively easy recovery. But people who can't put on that programmers hat may be significantly impacted. That group includes clients of said programmers who self-maintain. I'm all for growing the economy but you may want to consider how changes impact the broad spectrum or how/when they are communicated.
One recent example of this is the removal of the borders and margins from image editing capability of the visual editor. WordPress has grown to the point where sharing that change before it happens would have been helpful - not removing it even more so.
Managing growth is a challenge, thanks for letting me share.