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Turns out MarkDownify messes up the stack - it assumes the last thing (link) pushed to the stack is the url of the link when parsing. So if you add additional tags to the stack (in this instance an image), it thinks this what the link should point to.
The stack contains other details - attributes, reference ID (1 and 2 in the above) - and this mix up causes the above error.
As posted here http://wordpress.org/support/topic/close-but-not-polished?replies=3#post-4032749
Causes the MarkDown to be corrupted and the following error:
The post previews fine so the problem lies in the HTML -> MarkDown converter.
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