The rule of thumb at a previous job was if the shell script is longer than about a page then consider if another language is more appropriate. That seemed to se

The rule of thumb at a previous job was if the shell script is longer than about a page then consider if another language is more appropriate. That seemed to serve me well and I had dozens and dozens of personal shell scripts to smooth over rough edges of everyday tasks. It's also obvious when you start needing features like more than simple usage or flags or parsing html. I haven't had all that much experience with Python 3, but for the 2.x series there were often tweaks that needed to be made either with code or libraries when moving between new releases with a large code base. Lastly, Python just isn't great for making one-liners. It might be a personal quirk, but that's my favorite way to iterate over an problem. With all that said, I do really like Python and use it heavily.