As a systems engineer, I've always found it challenging to maintain a sane python ecosystem across multiple hosts.
1) use system python -- if you can. Now with python3.4 and 2.7 in stable, that's the easy bit.
2) If you can't do 1), use backports and/or manually backport
3) If you need python-packages that depend on c-libraries, use "apt-get build-dep python-foo".
4) use a virtualenv, or several virtualenvs, eg:
virtualenv -p python2.7 myvenv
./myvenv/bin/pip list -o #list outdated packages,
# typically that'll mean you first need to:
./myvenv/bin/pip install -U pip #possibly also setuptools
This works for most everything -- except perhaps for pygame, which is exceptionally gnarly.
 Manually backport, the easy way:
echo "deb-src http://httpredir.debian.org/debian\
sid main contrib non-free" \
apt-get build-dep python3
exit # No need to build as root
apt-get source python3 # this assumes sid has a version
# that'll work for you
dpkg-buildpackage -uc -us
sudo dpkg -i python...deb
I'm assuming your systems engineer perspective is colored by RedHat (and others) packaging python-ldap at the system level and then leaving you to your own devices for everything else.
C bindings are really convenient, but then you have to worry about dynamic linking. Are you sure Python is linked to the same OpenLDAP library that NSS uses? Hence, system versions of some Python packages, but only where other system level dependencies are an issue.
I think some of the problems were self-inflicted by trying to use Python on a Mac with no package manager, and on Windows. Things will get easier on the Linux side with Python 3 in repositories now. But it really seems like a fairly common pattern for languages / programming environments is to install the languages package manager and upgrade packages separately from the OS package manager. For whatever reason this seems like a bigger headache with Python than others.
But seriously, mirror your production environment for local development and testing. This is all comically easy with VMs, you just need to alter your workflow.
If pip doesn't work on Windows then it shouldn't ship on Windows. This isn't Windows' fault.
Granted this was recently, under windows 8.1 (tried it mostly for fun, and so that I have a decent calculator (ipython) on hand when I boot up in windows).
I was also pleasantly surprised, building python C extensions under Windows is easy. Building some of the C or Fortran dependencies, on the other hand, might be not.
Pip will drop ipython in the scripts-folder too -- so that where one can grab a shortcut. Or just (after restarting python):
IPython.start_ipython() # Ed: not .start()
There is a clear lack of _direct_ and _concise_ documentation about Python packaging. Something between overly descriptive reference documentation which nobody reads and "copy-paste this setup.py" that teaches nothing of substance.
Let me use the OP as an example:
"Wheels are the new standard of python distribution and are intended to replace eggs."
One important thing to remember is that packaging is a means to an end. Nobody gets excited about packaging so nobody wants to know too much, but also not too little that thinking about doing it instills feelings of dread.
PS: This applies to other packaging scenarios too. I've seen people fall to their knees when faced with building Debian packages for deployment (ending up not doing it at all), RPMs, etc.
Python's virtualenv is a lot more stable than the various hoops one goes through with eg rvm. On the other hand, if you needed/wanted to use more than python2.7/python3.4 -- it might be a bit harder to juggle many python versions than it is to juggle many ruby versions with rvm.
So the problem bundler/venv solves becomes a solution to 95% of the entire problem, rather than just 50%.
If by packaging you mean deployment, yeah, it's a mess. Only in the sense that you can't just FTP you application to any old server like you do with PHP projects.
It'd be nice if Python for the web "just worked" but it really isn't that difficult to get things setup (Nginx, Gunicorn, PostgreSQL, etc.). Also, there are a lot of reason not to want a canned PHP-type setup.
We have a policy to never bring-up servers by hand. You capture your setup and configuration in Ansible scripts, document them well and things just work. Then use Selenium to confirm that all is well with a basic test application. Life is good.
Python is a friggin' nightmare by comparison. Some trivial low-complexity operations can take insane amounts of elbow grease due to missing/outdated libs.
Pip does a remarkable job of magically getting and compiling missing c/c++ libraries, and works great in tandem with virtualenv.
From that perspective, I can see the OP's point. For most of Windows history, if you needed a library installed, you'd install it. Every installation was accomplished through the familiar Windows installer. If you needed a newer version, you installed it. There was process, and one target.
Now take modern Python. A new layer has been introduced, where you may run every project in a new target, or through the 'default' install. In addition, you have libraries and packages that may be installed through one of several different installers or processes, most of which are different than the OS's package management, and which aren't necessarily compatible and aren't tightly managed. This is on top of multiple python versions that may have to be installed.
I can see where he's coming from.
That being said I love Python and I respect the work that has been done to allow such a vibrant user base.
Have you tried setting $JAVA_HOME and restarting? rimshot
Here's a good overview of real world issues: http://lucumr.pocoo.org/2012/6/22/hate-hate-hate-everywhere/
(I'd imagine the core team thinks Armin should just embrace Python 3 already. And some of the details have changed since this post, naturally.)
I help co-maintain salt, a config management tool which he used and contributed quite a few bug reports to.
I've had a few issues over the years, but absolutely no showstoppers, and in no way any "disater" much less an "absolute" one.
Compare this to how languages like Go, Rust, Ruby, and Julia handle packages and dependencies and Python is an absolute disaster. Even if there are answers to the above questions, as a fairly advanced user I have no idea what they are, and I have done plenty of research.
> How do I upgrade all packages with Pip?
I don't know how to upgrade all packages, but I that's not something I want to do because I want to control which packages I upgrade. To upgrade a single package you can do
pip install --upgrade packagename
Egg is a package format. setup.py is a build script. pip and easy_install are package management tools. You use setup.py to build eggs that you install with easy_install or pip. You can also install directly with setup.py, but that's not something you'd generally do. pip is a better, more recent installation tool than easy_install.
> How does pip manage to break dependencies?
I'm not sure what you mean here.
> Why does no standard way to manage packages come pre-installed?
I guess the answer is because no one had bothered solving this issue until recently. Starting with Python 3.4, pip is included by default. See https://docs.python.org/3/installing/index.html
> How do I pin packages at a version?
You list your packages with their version numbers in a requirement file that you can pass as an argument to pip. You can use pip freeze to get a list of currently installed packages with their pinned version numbers that you can include into your requirements file.
> Why is there a need for virtual-env to exist as a separate project?
No need for that, it just hasn't been integrated in the standard distribution until fairly recently. Starting from Python 3.3, venv is included: https://docs.python.org/3/library/venv.html
> Compare this to how languages like Go, Rust, Ruby, and Julia handle packages and dependencies and Python is an absolute disaster.
Absolute disaster is a bit strong, but it's admittedly not as good as the other languages you mentioned. I think every Python developer who knows other languages will agree. That doesn't stop us from getting our job done though and the situation is improving.