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Coupled with the tips in the comments about COMPRESS_OFFLINE, you could look at django-staticfiles’ storage stuff. You can host the static files on amazon s3, for instance, so hosting it all on one static-hosting server and using that from all your servers could also be a nice solution. You wouldn’t need to do anything with the static (and compressed) files on the individual servers.
Alternative solution regarding the multiple servers: I’ve made a custom fabric (docs.fabfile.org) script that installs/configures stuff on our servers. I’ve only recently started using coffeescript and less, but those two are definitively ending up in my fabfile. That solves the installation problem for me.
(Alternatives to a fabfile are things like a custom debian package with standard dependencies. Or chef or puppet or something similar.)