Seconded. Python, even with virtualenv stuff, has never been bad. There have been a few things that have been annoying especially when you need system libraries (e.g. libav for PyAV to work, etc.), but you have the same issue with every other ecosystem unless the packages come with all batteries included.

To be fair to the GP comment, this is how I feel about Ruby software. I am not nearly as practiced at installing and upgrading in that ecosystem so if there was a way to install tools in a way that lets me easily and completely blow them away, I would be happier to use them.