This is a solved problem with a really bad case of "Not-Invented-here" in the python community.
What's funny is I'm pretty sure gems/bundler and npm/packages were heavily influenced by pythons plethora of crappy attempts (eggs, distutils...etc) at package management.
Anyone who's worked with all three of those would tell you that this isn't yet a “rest on your laurels” situation.
There are improvements to be made to all of them but gosh python is a complete mess in this regard.
Every solution has drawbacks, but python's solution has almost every drawback.
Another illustration, in reverse: the Chinese chopsticks are among the simplest tool you can imagine, and it requires a somewhat steep learning curve, but once mastered it is really the most powerful food grabbing tool ever invented.
The Chinese brush is of the same nature: extremely simple, very hard to master, and very powerful (expressive) once mastered. Just like the violin (and VIM, and git, etc.)
On the other side of the spectrum you have the synth, IDEs, Google search, etc. Simple UIs, simple to learn, but internals are very complex.
Actually it is even true for music instruments: A piano is very complex inside and can be played relatively easily, while a violin is much more simple in the fabric but much harder to play.