Was contacted by hosting company:
We just had another ticket in regarding this and were able to correct the issue. The fix is outline below.
We adjusted the value to FcgidMaxRequestLen 1000000000 in the apache config as outlined > http://forums.cpanel.net/f5/config-mod_fcgid-related-maxrequestlen-timeout-214031.html#post1008351
If anyone is still having this issue let us know via a ticket and we will be happy to adjust the value for the server your on as well.
Thanks
The topic can be found here: http://forums.asmallorange.com/topic/16354-django-and-media-uploads/?view=getnewpost
Just if anyone views this question in the future. Glad to know it wasn't my fault, at least. Too bad it took so long to resolve.