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skreutzer, I do not know, but I think your project is very ambitious. I have no problem with that, but this could complicates things, at least initially.
By the way could you summarize point by point, in list form, the main aspects and goals of your project? (dickloraine has worded some good questions about it). You know, sometimes trees hide the forest!
I think the idea suggested by roger64 is very good, and if that is the case why not start with the 'easy' stuff?
Let me explain. Writer2LaTeX/Writer2xhtml has not been updated for some time, so why not start with this update if you can do it? The source code is available and can be modified within the GNU LGPL if I'm not mistaken. I am convinced that hardcore Writer2xhtml users will be happy to suggest you what should be improved.
Another positive aspect of this suggestion is that it allows you to put aside the issue of free and non-free os/apps since LibreOffice or AOO are cross-platform.
Finally, an another interesting thing to do would be to create, as you suggested yourself, a kind of wizard which will guide users to better understand the enormous interest of semantic encoding. With suitable templates and some macros for example, the end-user would be offered to create a project (within LO or AOO), step by step, and show him what to do to properly encode his or her documents.
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