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Wasn't iOS8 going to support extensions for mobile Safari, i.e. move in the direction of more openness?
Yes, it will, as far as I know. That's a tangential discussion though. This article deals with the crippling of the native <input type="file"> element and File API support in iOS.
Is that for web views embedded in apps? I can't recall mobile safari or any other app providing a file upload option in a browser view. I was hoping that extensions would enable this feature.
Since iOS6, the <input type="file"> element has been supported, which allows the user to select a file or files from the underlying OS.
Just tried this in Safari on iOS7. That element enables choosing of a photo.

To access a file from the underlying OS, do you need a jailbroken device?

iOS doesn't really have a filesystem. You can only store photos and videos, which are accessible via an <input type="file">.