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Why is it painful?

Because if not run in a container, you should put things that upgrade Requests in a venv at least otherwise you may end up breaking apt.

But shouldn't you always use a virtualenv anyways?

Project-wise? - Most definitely! Globally? - Not common practice, but also preferred to avoid collisions.

You might consider taking a look at Twitter's pex. Python supports importing and running code from zip files. pex aids in bundling python code and its dependencies into an executable zip file.

Unfortunately that's simply not the same. Python libraries many times still require header files to be present, which means on a host you want to install PyOpenSSL you must also install libssl-dev, which means you also much install python-dev... etc etc. Don't get me started on using gevent.

A container is the only sane way to package a python service, but that's not _nearly_ as convenient as a statically compiled binary.

Legacy CentOS too