1. I rarely have problems with package management in Python. I know pip has flaws but it's not enough of a pain point for me to see it as an issue. 2. I'd say

1. I rarely have problems with package management in Python. I know pip has flaws but it's not enough of a pain point for me to see it as an issue. 2. I'd say Python is an easy match in this regard 3. Agreed about the docs - I still find the organisation of Python's docs a bit peculiar. 4. Handy data structures, you say? I think Python might have the edge here. It's strange you don't mention PHP's biggest strengths: deployment and learning curve: You can begin on almost any commodity hosting with a simple text editor and no knowledge of Unix internals. The amount of extra stuff I had to learn to be productive in Python was huge at the time. It's got a bit better now with various simple deployment options but PHP still wins out for the beginner.