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Geez, installation of the enterprise python software seems to be very complicated...
Now it’s not anymore thanks to the Installer and all the improvements we did (as explained at the blog post).

But normally it is, yes.

packaging and distribution are definitely python's weak points... for deploying to (internal) servers i've really been liking docker.
I have worked with PECL, CPAN, and I find pip to be quite easy and virtualenv pretty cool. Arguably npm is better, but relatively speaking, I think it is py2/3 split that is pythons weakest point.
Here's my old school setup:

Deployment: `easy_install -U` from a local pypi

Packaging: `setup.py bdist_egg` and `setup.py bdist_wininst`

Dependencies: declare in setup.py, fetch via yolk

To test if everything works, just create a blank virtualenv and easy_install.

This has been working fine for me for years on Linux and Windows.

Do packages with dependencies in C still require compiling during pip install?
While pip does not support binary eggs, easy_install still does. If you want binary distribution with pip you need to use wheels (as you are, of course).
Can you talk about Windows python packaging - I have been struggling with some of that for some time.

Did you ever have to package stuff like DLLs as part of your code?

Seems like a bad idea to delete the existing sandbox before downloading everything and installing.

A better idea is to move it to a temp location in the first step, and only delete it after the new version has installed correctly.

I still install binary eggs and easy_install occasionally. Why didn't those fit in with pip?
For hysterical reasons, pip has never supported binary eggs. Wheels are the replacement of the future!