Thank you very much for taking the time to answer in such detail. It does confirm my suspicion that most of my use cases are already adequately covered by JS/TS/Node and that there's not some killer hidden feature that I am missing.
The links you sent in particular answered a lot of questions for me. Seems like one of the biggest draws (for me at least) is that python is slower to change over time. That cannot be understated and is my biggest frustration with the JavaScript world. That is, the unending need to learn the new "Obviously Best Way" to do things every 12 months or so. It gets exhausting.
Not an expert but would recommend you to look at pyenv with virtualenv from the start. This allows you to use python3 version of your choice in virtual environment based say per project etc. Obviously, this landscape has been changing rapidly lately and other people might recommend different tools, but for manual (or automated) server deployment I like this - I can test new versions of libraries and python (3.7.2 ;) and switch between them super easily without affecting/breaking each other.
The links you sent in particular answered a lot of questions for me. Seems like one of the biggest draws (for me at least) is that python is slower to change over time. That cannot be understated and is my biggest frustration with the JavaScript world. That is, the unending need to learn the new "Obviously Best Way" to do things every 12 months or so. It gets exhausting.
I'm naturally curious so I'll keep learning python. Can't hurt right?