Django has a lot going for it in terms of simplicity but it lacks most of Rails' advanced features and timesavers. In my experience it sits somewhere between Sinatra and Rails
Also, having to deal with Python packaging is a world of hurt. No thanks. There's about 16 ways to package and distribute Python, and they all are half-complete and a royal pain to deal with. Ruby's packaging isn't perfect, but it's a thousand times better than any of the Python packaging solutions out there.
Package management is a hard problem, but we know that good and adequate package managers do exist. I'm not sure why more effort hasn't been expended by the Python community, particularly since it's often the first thing a new user will encounter when picking up a language for the first time.
I use Pipenv currently, but only because it's the best of a bad lot and would jump in a heartbeat if a serious competitor came along. It has its own set of problems (slow, young and idiosyncratic) but offers me at least two things its predecessor didn't: separation of production/dev dependencies and seamless integration with different versions of Python, both of which have been available in Ruby since I started programming in it.
This is a perfect exemplifies my experience with both languages: I have found while Python might be better at a lot of things, the user experience is invariably superior with Ruby efforts and I wish the Python community would put more effort into this area.
