I was able to do this with WPAlchemy and its function have_fields_and_multi(). It allows for adding an arbitrary number of sections (by means of an ‘Add New’ button), called groups, that can contain all the metadata I needed, including links to images which can be added using the Add Media dialog which was made easily accessible by WPAlchemy. All metadata is then saved and linked to that post. WPAlchemy is pretty easy to use once understood. I found the documentation too brief in parts. In any case I found it makes designing posting interfaces much easier.
As I understand it groups can not yet be nested but this could come in a future update.
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