I think that scale is a little misleading (well in my opinion) I think reading their article suggested better labels - User Focused -> Developer Focused.
For me SilverStripe would sit roughly around the Django position. The framework is there and you can build rather complex apps within it (3.0 the framework will run independent of the CMS) but there is a lot of helpers for developers, even some which has been 'inspired' by Django itself, such as model admin and some of the form scaffolding.
The roadmap and timeline for 3.0 is up on open - http://open.silverstripe.org/roadmap. The core team don't try and put dates on anything too far ahead in the future (as we're pretty hopeless at keeping to deadlines!) but you can see relatively how it's coming along.