This idea needs some help. Or maybe the hook. I don’t know:
With a digitally scanned copy of a Gregg Dictionary, it seems to me that the only major hurdle (besides copywrite?) to having a program that translated type into Charles Rader’s Gregg would be a method of batch-analysing the dictionary page images into sets of type-to-outline pairs. With a table matching type-word to outline-image, writing a translating program would be straight-forward.
The method would be brutal (compared to something like psetus’ real-time translator, Greggory); the static database would be irritating to some degree. But the Simplified dictionary, at least, has a pretty big lexicon. Gaps could be filled in by a skilled writer to allow for most of the ordinary prose in your Steven King novels. Don’t bother trying to convert Finnegan’s Wake, of course.
Can anyone imagine a method of doing that kind of batch-programmmed image parsing? I can imagine the mechanics of converting from word to image, but I don’t know anything about image manipulation.