I agree with RMS philosophy and respect his purist ideal immensely. I also respect how he practices what he preaches to extremism. I think his purity and extremism is needed to advance the idea. But reality/practicality is best served by walking a middle ground. use as much free software as you can but also use proprietary software when it clearly is a better or necessary choice.
I don't think Ubuntu will ever overtake Windows unless it achieves this middle ground more effectively. Currently, the company that is practicing this "middle ground approach" is Google. Chrome, Android, etc. And they are very successful.
If Ubuntu moved more to the middle ground it would be more competitive with Windows.
USA laws are really messed up. They stifle innovation and cater to wealthy people at the expense of creativity and wider innovation. I don't see how that's going to change anytime soon.