Nice post, tons of great advice. However, I have to say that the title is wrong. There's nothing django specific about any of those approaches.

I've tried django-compress and it was a nightmare, the old style synccompress was actually easier to setup and get working for some reason.. Was hoping for a better rolled solution.

Also, the part about cloudfront isn't written very clearly. I had to stop for a moment and think about what it meant. Great idea nonetheless. S3's gzip support sucks. For some odd reason (I don't support IE6..) the gzip from S3 was breaking on IE9. Worked fine on 8 and 10. Broke on 9. =/