I prefer Python over Ruby as a language, but you are correct gem ist superior to pip. Take a look at "pip-tools" if you haven't already, it eases some of the p

I prefer Python over Ruby as a language, but you are correct gem ist superior to pip. Take a look at "pip-tools" if you haven't already, it eases some of the pain. For web-dev Rails is more stable, more modern and has better maintained library ecosystem than Django. Django is okay-ish but can't live up to Rails. Django still lacks some stuff that i feel it should bring with it out of the box.... dev/test/production setups, asset compilation etc. On the other hand, if you don't need a full blown web framework and are looking for something more minimalistic, Flask is awesome.