In the Roadmap there is this item: Modular File Storage Locations, and a plugin for Amazon S3 file storage (along with the ability for developers to package and distribute their own for other cloud storage providers.)

This seems like it would be extremely beneficial to the welfare and advancement of C5, and on top of that I personally would use it on several dozen sites I've got running.

Is this something that we should be expecting in the future or should I be looking for a different solution for file storage?

There was a forum post a while ago about using a CDN with the file manager, but it never had a complete sustainable solution.

What would be the coding challenges that would need to be overcome? and would it be posable to have the cache and other static items automatically transferred to the cloud.