I think the lifecycle of a Linux user often goes like this:

1) I don't understand this

2) I'm starting to understand it!

3) Now that I understand it, I can play around

4) I will tweak it to be the ultimate system for me, that works exactly how I want, and (often) it will look like I'm hacking while using it

5) I'm starting to feel the limitations of the system. The hackerish GUI no longer appeals to me, because I see it as just some OpenGL and Ncurses commands

6) The Mac Mini is looking rather nice...

I think DHH is on step 4. Will he go to 5&6? Maybe not, because his reason for going to Linux is due to unhappiness with Apple's app store behavior. I hope he finds a new Linux user path I didn't think of.