I have been giving this a lot of thought for months. I believe it would be very useful to be able to relate files to positions. Whether it be an audio/video recording of thoughts, a copy of a video lecture, a document, a picture, a relevant .pgn file for review, [EDIT: a website], or even a FEN string which would invoke a sparring match with the user's engine.
The file aspect of this could be done through hyperlinks, i suppose, at a bare minimum. A much more time intensive solution would require a method to create a private resource database of files within the CPT/repertoire directory. I hope you like the idea.
Matthew Freeman