I think the question at hand is not where to store and serve the media files, but how to write an app that can easily support accessing media files from different urls. I had this same issue between my development and production apache servers:
Dev Site localhost/mysite/images/whatever.gif Production mysite.com/images/whatever.gif And even the occasional development on my laptop on the road localhost/~myuser/mysite/images/whatever.gif This was never a problem in my previous dev environment (php) because I'd always just use relative urls like: <img src="images/whatever.gif"> But with django's more flexible url mapping, I need to make all the links absolute. The most frequent suggestion is just to define a setting such as the MEDIA_ROOT that can be set to "/images" on my production server, "/mysite/images" on my dev and then "~myuser/mysite/images" on the laptop example. Looking at ruby on rails, they seem to have some template tag equivalent that does url generation for you automatically (stolen from the rails tutorial): <%= link_to recipe.title..... Perhaps django could use something similar?
