In my experience, most Python projects are quite hard to scale or maintain precisely because they weren't written with a proper domain-specific approach. You'll be pressed to find a medium size python project that uses a database and doesn't use the leaky SqlAlchemy/Django ORM abstractions where data and operations on data are "the same thing"; On the same vein, any medium sized project with dozens of, hum, "models" will lead to files with thousands of lines. And don't even get me started on using an HTTP application instance as a container for configuration, usually included in every other piece of logic under the sun.

You can easily guess I'm not a huge python fan (nor java, but it so happens I work daily in medium-sized projects in python), and I do have problems with the "idiomatic/pythonic way", but lets face it - python, while very expressive, is often so convoluted that static analysis of code isn't even possible. If your IDE is not able to quickly determine a given var type, you expect the average developer to be able to do it?

Python is - first and foremost - a prototyping language, and an excellent choice for glue code. For big applications, you will actually learn to enjoy the bitterness and complexity of Java over python, and small stuff like strict typing.