So I'd be curious if someone can comment how VSCode compares to PyCharm wrt language aware features, such as: contextual selection, refactoring, finding usages, method/function extraction, auto-fixing, etc...?
That's mostly it. PyCharm is easily going to squish VSCode at the features you listed.
1. Same key bindings and similar functionality out of the box across a lot of languages.
2. Language injection, i.e, have a string in your python function containing sql or html or js or anything.
3. Generally better than the competitors. For python that may not be true, as python is highly dynamic and not possible to do too much static analysis, but Pycharm does a good job.
4. All jetbrains products are very well integrated with the ecosystem. e.g, virtualenv, jinja2 out of the box.