What's wrong with PIL on Ubuntu? If you're running into needing to repoint JPEG_ROOT/ZLIB_ROOT - I've started avoiding that by symlinking where PIL expects things to be to where they actually are). Works a charm, and avoids using --system-site-packages.
I used to do this, but it feels like a suboptimal solution. I could use Fabric to ensure the links are there but it adds more complexity to the setup:
a) Another step to remember
b) Requires a compiler on the production system
c) Requires you to manually resolve the image library dependencies
Multiplying that across multiple packages can quicky become a headache. It's much easier to let the OS package manager deal with this, and will make your system more robust over time.
