Since your IDE Provides you with a "Navigate to" functionality and you have some control over namespacing within your classes then the below benefits of having multiple classes within the same file are quite worth it for me.
Parent - Child Classes
In many cases i find it quite helpful to have Inherited classes within their Base Class file.
It's quite easy then to see which properties and methods your child class inherits and the file provides a faster overview of the overall functionality.
Public: Small - Helper - DTO Classes
When you need several plain and small classes for a specific functionality i find it quite redundant to have a file with all the references and includes for just a 4-8 Liner class.....
Code navigation is also easier just scrolling over one file instead of switching between 10 files...Its also easier to refactor when you have to edit just one reference instead of 10.....
Overall breaking the Iron rule of 1 class per file provides some extra freedom to organize your code.
What happens then, really depends on your IDE, Language,Team Communication and Organizing Skills.
But if you want that freedom why sacrifice it for an iron rule?