5👍
Go figure, that I would solve this 5 minutes after posting. I am not sure what the true issue ended up being, but that is how I solved it.
Since installing libjpeg with aptitude, I looked into installing PIL with Aptitude rather than Buildout.
What I ended up doing was:
sudo apt-get install libjpeg62-dev
sudo apt-get install python-imaging
Then I removed PIL from my Buildout, re-built my project and it worked. Now that PIL and libjpeg were installed through Aptitude it appears as though this resolved any issue PIL had finding libjpeg.
Source:stackexchange.com