> Does anyone have any suggestions on tools to look at?

It's not ruby but...python's docutils uses plaintext files and 
reStructuredText[1], which is pretty similar to markdown but fuller 
featured.  It can output to html, latex, and xml.  It's what I use for 
most of my python coding.

[1]: http://docutils.sourceforge.net/docs/user/rst/quickstart.html

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