Well you really shouldn't be serving static content through Django, you should be serving it through a CDN. If you use something like Django-Storages for upload

Well you really shouldn't be serving static content through Django, you should be serving it through a CDN. If you use something like Django-Storages for uploads, it'll Just Work. I'm not guaranteeing that everything will work out of the box on the first try, but I bet you'll be very close. You will have to make a few design decisions, but if you're making the right ones it should just work. At the very least it should be far, far easier that GAE. (The one thing you'll have to watch out for are C-extensions, which, for now, require that you do your deployment from an x86_64 machine.)