Yehuda's approach reminds me of the early days of webdevelopment where you could install a WAMP stack with one click on your windows systems. I never liked those one-click-installers—you don't know what happens to your system and deinstalling was a nightmare with still running db servers somewhere for years.
You can't wipe away Rails complicated entry with such an one click-installer. After you installed Rails with one click things aren't getting easier your still have to figure out next steps and which frameworks to choose (i.e. ERB or HAML, SCSS or LESS, MySQL or Postgre, etc.). Or something breaks within rvm: with an yehuda's approach you are completely clueless because you don't know anything about rvm, gemsets because the installer did all the work for you.
Sometimes there is even too much magic in Rails. I am still wondering if ActiveRecord is too much abstraction and if there are better more direct ORMs like DataMapper, I am used to ActiveRecord but still I can not fluently create data models, there's always something I forget, using the plural or singular, saving the updated migration, rolling back the migration, etc. Otherwise it's far beyond any ORM from other Frameworks I have ever seen in terms of speed. And its usage in Ruby is very consistent. Also Rails shell commands are very consistent, once you understand the rails syntax (like rails generate or destroy something you can quickly build anything in minutes), I tried several times to find something similar with python/django but there the entries seemed to me even more complicated, don't follow any system and felt restricted, i.e. Django's automatic Backend (no offense, i know not enough about django and python to say anything serious but that was just my first impression).
Another last great example of Rails: once you managed to install Rails, just put haml, less, less-bootstrap-rails and simple_form in your gemfile and run bundle. with this setup you can build web apps in minutes with perfect design and they are fully customizable. some years ago you needed hours or days to get to similar results. It takes time to get there but once you are there you have the power.
this pace and variety in the rails ecosystem comes from so many talented people who contribute. trying to set one standard for how things are done would slow down this pace.
finally, I think that Yehuda doesn't want to raise money, he just wants to get attention and the approval that he had the right idea.