Problem enabling the user to edit Markdown and displaying the HTML output (WMD Editor plugin for WordPress)

that is the normal way for it to work, when you save it turns the markdown text to html, so when you edit you need to reverse the html back to markdown text.

there is an outdated plugin that has most of the functions you need it http://wordpress.org/extend/plugins/markdown-for-wordpress-and-bbpress/
that would be a good place to start.