Hello Neil Mercer,
You can achieve such functionality because Sitefinity has the documents/images/videos infrastructure in place, but you need to create a custom widget which will be taking care of the uploading and sorting the image in the right library.
Please take a look at our documentation
( the part about the images ) and also in the SDK samples which have a number of different controls and widgets which might give you an idea how to build your custom control so it suits your needs.
the Telerik team
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