After listening to the recent Hanselminutes podcast with Martin Fowler and David Heinemen Hanson, it dawned on what the difference between the two camps really was.
Microsoft is attempting to be all things to all people, and so therefore, they are creating tools that can do everything for you in the easiest way possible. The Ruby on Rails guys have decided on some best practices that preserve the aesthetics of the code and expect that you will conform to that standard. I think both are very admirable things to accomplish.
The point at which this diverges though is that while Microsoft's plan is to be on every developer's desktop, the RoR guys could care less if you use their framework. If you don't like having to put your model classes in the model folder, then don't use their framework. If you dont like having convention over configuration, Ruby on Rails isnt for you and you should go find something else. Guess what, the RoR community doesnt care.
The RoR community is not going to sacrifice the aesthetics of the code just to appeal to more developers. The people that are drawn to Rails are the developers that do care about these things, and I think thats why a lot of the alpha geeks are looking at and working with Rails. The RoR community has grown to where it is because of the grassroots efforts of the people that are passionate about code and what it looks like, not by drag-and-drop coders.