Wow - good info and good questions.
You're pursuing what I consider the hardest of all musical challenges (other than raw composing).
I'd hope others will respond, but here's my 2 cents worth:
Ted moved in and out of styles and so on because he knew them as discrete things (i.e. Bach, Big Western Scores, etc.). He knew what made those sounds unique - both the harmony and rhythm.
So, one could argue you might pursue your goal by picking a style and studying it. The Bach improvisation, for example, was one area he taught quite a bit. Folks like Mark Thornbury are quite familiar with that.
So I'd suggest you try to 'quantify' the style or styles you're interested in, and then find ways to capture that on the instrument. From time to time I've visited the impressionists like Debussy - I found it challenging to say the least.
An alternative, which is to explore chord forms etc on the instrument, is one I find to be too hit or mis and too time consuming, so I would say DON'T do that.
The problem is that most players didn't float between musical era's as effortlessly as Ted. You may have to pursue a pianist who approaches it that way.
In the short term, pick one or two styles you're really ready to chase, and then ask here in the forums for anyone who can help in those styles and/or with any Ted pages they might have.
Because Ted's teaching pages were often targetted to a particular student, you may get only pieces of the puzzle so I'd encourage you to get a perspective on the style to guide you. Some one here may be able to recommend well focussed material.
Again, I'd say "Style first, then the instrument." That's a drag for some because its theory and logic heavy, but I'm not sure anyone has really quantified different styles, crisply, for use in guitar arranging. Ted seemed to have the lead in that area.
I would say that his books are probably not too useful regarding this subject.
There are recent audio lessons posted that have ted explaining Gospell and Blues that are a good start on those areas.
Ted had pages that summarized musical styles, by era - those might also be a very high level guide.
When you figure this out, let me know. I'll come over for lessons . . .