The biggest problem with this "omakase" attitude is that it's causing Rails developers to miss the boat on many new developments in the state of the art in web app development because legacy is now baked in via opinion. 37Signals hasn't been the forefront of web-app design for a few years now. There are plenty of single page web apps out there that are far more responsible and present a better user experience than tools from 37Signals. Don't get me wrong, they are still decent, but they aren't demonstrative of what is achievable insofar as excellent user experiences are concerned.
Maybe this has changed, but I spent a year working on a single page webapp built on Rails and the asset pipeline was excruciatingly painful to debug to get your javascript and other assets handled properly.