For me personally:
* I like Rubygems & Bundler more than Pip
* I find the split between Python 2.x and 3.x to be obnoxious
* Python whitespace indentation bugs me a lot
TL;DR -- Python isn't much different than Ruby in terms of what it can and cannot do. Personally, my new favorite language is Elixir, which does a whole bunch of stuff neither Ruby or Python does particularly well.