Forbidden after enabling SSL
Well, that was frustrating. The issue ended up being a simple typo in my second VirtualHost definition. Specifically, the WSGIScriptAlias should be WSGIScriptAlias / /home/administrator/Documents/MyRepo/MyApp/MyApp/wsgi.py not WSGIScriptAlias / /home/administrator/Documents/MyRepo/MyApp/MyApp.wsgi.py. The only difference is a period where there should have been a slash, between the final MyApp and wsgi.py. Hopefully someone else will read this and be spared the hours of nonsensical debugging.