One thing that is direly needed in pip is a way to specify system package dependencies. The way packages fail right now if you're missing something like libjpeg

One thing that is direly needed in pip is a way to specify system package dependencies. The way packages fail right now if you're missing something like libjpeg is cryptic and nasty. Users need to know that they need to "apt-get install x" or "yum install y" without googling for that cryptic error message. Compared to that, I'd consider the overgrown setup.py interface or need for a MANIFEST.in file to be barely even a problem. I tried writing a package that took care of specifying unix packages in a distro independent way (https://github.com/unixpackage/unixpackage https://github.com/unixpackage/unixpackage), checked for installation and asked politely via sudo to install if the package wasn't installed. However, in pip, the "ask politely" approach became impossible after v1.5.6 because of this bug/decision: https://github.com/pypa/pip/issues/2732 https://github.com/pypa/pip/issues/2732 (a sudo prompt came up but it was not possible to give an indication to the user of why it was there, so I gave up on the idea)