Django Http404 and DEBUG mode catch 22

You can simply pretend you are in production. Run:

python manage.py collectstatic --noinput

To have all your files copied to STATIC_ROOT. Then, temporarily add the following to urls.py:

urlpatterns += patterns('',
    (r'^static/(?P<path>.*)$', 'django.views.static.serve', {'document_root': settings.STATIC_ROOT}),
)

You'll have to run collectstatic each time you make a change to any static files, so I would suggest live-editing in something like Firebug and then saving the finished product. Also, remember to delete the static directory and remove that line from urls.py when you're done.