And look where Python is on the various distributions. Behind. Constantly behind. The day a distro decides to use Ruby for system level stuff like they used python is the day that Ruby on that distro is DoA.
Of course it's behind, and that's what end users want. Bleeding edge is called that for a reason.
Python on Debian works fine. There are a whole bunch of apps written in old versions of Python that just work, and you never have to fiddle with dependencies, and you never break them.
If you want to develop in Python, you install virtualenv and you get a bleeding edge setup exactly like you want it, and it doesn't break your working apps.
The OS-packaged Python version is designed to support the OS-packaged Python applications. No more, no less. The whole point of having a software distribution is that it's curated such that it all works together. Your code? Not curated, so no guarantees. Module Y? Maybe curated, maybe not.
Getting "running code on the server" is an edge case, not the primary goal.
You say that as if that's a bad point: what's the point of being always on the bleeding edge for the end user ? What do you think is the work of a linux distribution (or any packager, really). I am quite proeficient in python (which has basically the same issue), and certainly can compile it by myself - but this takes time, knowledge, and is detrimental to the platform in the end if that's required. There is no hard issue that I cannot solve by myself, but OTOH, as soon as I want to share things with other people, this is nightmarish because of versions issues, incompatibilities, etc...
Lots of people use python but are not developers at core, and having constantly changing things every few months is horrible. Imagine what would happen if everybody was working the same way: gcc in debian would be optimized for gcc developers, so you are always on the bleeding edge, and if your program crashes because gcc had a bug or temporary incompatibiliy, no biggie, right ? Same for kernel, etc...
The kernel is actually a good example on how to do things: the kernel itself changes quickly, but distros do the work of stabilizing things.