Ben, I’d be _very_ interested in a tool to convert Markdown to Trac’s WikiFormatting. It’s been a pain in the butt for me to keep two versions of wiki pages; I create and edit in Markdown locally, then have to reformat it for the wiki pages. Being able to write once and use it everywhere is what would be ideal!
Maybe another idea would be to ask Trac if they support alternate formatting (such as Markdown or Textile) as a third-party add-on to a Trac instance.
Aaron’s html2text looks cool, thanks for the link.