Contract opportunity: formatting outlines

I have a desire for some Mac OS X “glue” code, and I’m looking for thoughts on whether it would be affordable for me to contract the work. If this can be built for a small fee then I’ll be happy to contract for it. If it’s a bigger project than I imagine, perhaps I could float my small budget to someone who is interested in making this a shareware or commercial product. Perhaps my vision exceeds my budget, and that’s just the way it is. [End disclaimers.]
I use OmniOutliner for writing and organizing fairly lengthy documents, on the order of 15 – 60 pages. They get longer every project. I use Adobe InDesign to layout and format these documents. I love both of these apps and it’s the most productive writing environment I’ve ever had.
The most time consuming part of my workflow is applying typographic styles to the documents in InDesign. A 60-page document has headlines, body text, interview quotes, sub-headlines, section headings, footnotes, citations, etc. Here is an example workflow: In OmniOutliner, export the outline file as text-only, usually as a MORE document; open the InDesign template and load the text (get text); select all and apply the “body text” style; go through the doc paragraph by paragraph and apply the styles; if there are any character styles apply those last. When you apply styles you have to select the text and then click on the appropriate style in a palette. Styling a 20 page document takes around two hours and is very error-prone. When I’m done the index finger of my “mouse hand” is nearly numb from repetitive motion.
OmniOutliner has multiple columns. While I’m writing, wouldn’t it be nice to have a column called “Style” where I could enter the style name as I go. I would type the “Head-A” text, hit tab to the next column, and type “Head-A.” Basically I’m styling the doc as I create it.
InDesign has an SDK and a tagged text format – I haven’t looked at it but plug-ins rule the world in publication production so it’s probably pretty powerful. What I want is to import the OmniOutline document, or the text export, and if an InDesign style of the same names exists as the label in the column named “Style,” apply that style on import. This, truly, would be heaven.
A couple of approaches come to mind. The full-blown method would read the OmniOutline document directly as a legitimate InDesign “Get Text” format. A less intense approach might be an AppleScript to export the OmniOutline document as an InDesign tagged text document. The Perl-ish approach would be to take the output of the standard OmniOutline export and transform the text doc into an InDesign tagged text doc, or even a full-blown InDesign document. I’m sure there are other approaches that might be better informed as to the pros and cons.
InDesign SDK info: The “Exploded SDK” is browsable online.
Wadda ‘ya think? Is this a day-long project or a month-long project? Are there any existing plug-ins I could use? Your thoughts and proposals welcome!