Andrew, you are absolutely right about Automattic trying to improve things, but as you said — menu probably isn’t the place for innovation.

The only thing I don’t like about the new navigation is the fact that it is vertical instead of horizontal.

At the same time they have done an amazing job by testing and optimizing menu labels, which I think are now better and easier to understand.

Most of the OS X applications are good examples of the number of items which vertical (and application-wide) menus can have — for example, iTunes has three top level menu items out of which only one is expandable.