Updated this site. The photos in the blog post now upload a photo to MEDIA_ROOT instead of just being a link to a photo name and then searching for that photo in static/images. It's a very simple solution and I'm appreciative to the folks at Django for figuring it out.

I'm going to have to merge with the master branch and discard changes to the db on my home server. Hopefully I don't lose any posts. I think there may be a lesson in here about backing up databases.