This sounds similar to my journey with Python. For years, I used it as a go to for programs that were bigger than a bash script but smaller than an application

This sounds similar to my journey with Python. For years, I used it as a go to for programs that were bigger than a bash script but smaller than an application or service. I mostly wrote single .py files with maybe the odd module and avoided setuptools and friends. In the last year, I’ve been working on a larger library in Python, which has meant getting into the packaging and deployment tool chain and structuring a project with dozens of files, tests, etc. My background has been in mainline languages such as Java and C#, with excursions into Clojure, F#, etc. We adopted the new Python type annotations and they seem to increase the visual clutter of the language without delivering many benefits in terms of confidence or ease of development/code completion. Our library is aimed at data science, so I’m sure not many users will actually bother setting up the tools to do type checking. I do still appreciate Python, but I wonder whether my issues are due to our approach, my current level of familiarity with Python and the ecosystem or the fact that we’re working in the data science world which is new to me as well.