Or maybe you got the guy who knew how everything worked re-write it to function better than it had before, versus having core devs learn exactly how it worked and then implemented it.

To go back to your original question, of is Django pay for features, I don't know enough about it. But one place you could look into is the amount of corporate support Django gets. Maybe Rails has enough corporate support + people who want to work on Rails in their free time in order to get the features, versus Django. Sometimes you need to pay people to work on open source projects and the crowdfunded thing is just more visible than the corporate employees.