I've got several sub-websites that are basically html versions of powerpoint presentations. I need those files installed on every Azure web role of the parent application because the files MUST come from the same domain (there are dependent cross frame operations going on in a SSL environment.)

I would just add them to the project file and upload them, but that does not scale, these packages can be in excess of 5mb a piece, with a large number to exist eventually.

How could/should I think about pulling files from say, S3, or an Azure Blob, on startup of the role, and triggered manually by me when there is an update?

For the on-demand, the parent application is an c# MVC app, so I can use anything within that framework to trigger a job.