Sorry, you won't like the answer.
I've got the same problem:
There is no easy way to do this with static-served CSS files.
What I do:
- debug server, work locally, media served locally
- production server is hosted out somewhere commercial w/media on Amazon S3
- settings.py file auto sets MEDIA_URL (DEBUG, etc.) via hostname check (to differentiate production vs. local/home/debug)
- HTML files all have css links with
{{MEDIA_URL}} (+RequestContext
contexts for views)
- I like absolute path names, so an "update_s3" script:
(1) alters each css file is temporarily to fix
'url("/media' to 'url("s3.mydomain.com/media' and
(2) updates/uploads my /media directory to Amazon S3
I then go to production and do an svn update & touch the WSGI file & validate