Regardless of whether or not you choose to _deploy_ with Docker, _developing_ in Docker containers using the VS Code Remote extensions really solved all of Python's (and Javascript's) annoying packaging problems for me, with the bonus that you also get to specify any additional (non-Python) dependencies right there in the repo Dockerfile and have the development environment reproducible across machines and between developers. YMMV, of course, but I find this setup an order of magnitude less finicky than the alternatives and can't imagine going back.