django-sslserver is only for development purposes... I've not used django-sslserver, so I can't comment on it. I've used local apache server for testing.
It's not terribly difficult to configure apache or nginx for self signing or commercial certs. Though I do find google necessary for that chore.
I've used apache a couple of times for HTTPS: and there's been little to no magic getting the pages redirected. Browsers usually stay with the root, in fact you have to go out of your way to get them to point to
http://unencryped links.
I've use apache's mod-rewrite to ensure http: is redirected to https: for the appropriate paths/URIs, but that's for landing on the server, not keeping it straight after the fact, tho.. I suppose if you continue to have these issues, it could be helpful.