Who knows? Perhaps DHH doesn't follow jey's instructions to install ruby and start a rails project?
In any event web services like Heroku make it a moot point. I've yet to try it out but I can easily see the attraction when a trivial google search of "ruby install error" returns 100,000 hits.
I'm not claiming other languages are easier to install. I'm saying there is value in offering development tools over the web in a way that eliminates any need for installation.