Lots of great feedback thus far. Thanks all! A little summary of my favorite stuff thus far:

Andrew Johnson anj at aps.anl.gov on Mon Aug 15 15:02:39 UTC 2005 wrote:

My own approach would probably be to look at some existing and relatively straight-forward format such as RTF (or, I guess, HTML, although that probably covers a wider range of actual formattings), and attempt to write a "simplifying converter" - where markup has become bloated by export from a feature-rich editor, extract the general gist (e.g. "this is a heading") and create appropriate markup for that in Wikitext. While not ideal, a lossy converter like this would probably be fine for "initial import" conversion - you write the code in Word, export it mostly in tact (via RTF, or maybe just through macros) to wikitext, and then tidy it up within the wiki.

This would be great. It probably won't handle embedded images nicely, but that's probably pretty tough. This would solve the biggest portion of my current problems.

The edit-wiki-pages-with-an-local-editor problems seems like it might take a while to solve, particularly if it were done with MS Word.

In the meantime this looks to be the most promising mechanism at the moment:

http://search.cpan.org/~diberri/HTML-WikiConverter-0.30/WikiConverter.pm

I have yet to try and install it. I'm not thrilled it's in perl (presumably, being that it's on cpan.org), but I'll take what I can get.

-Matt