Phil, you have asked some excellent thought-provoking questions.
The short answer is "it depends", and unfortunately what it depends on is details of your lenses that I don't know. But perhaps I can summarize the issues so that you can do your own investigation.
The defining characteristic of optics that are telecentric on the object side is that the axes of the entrance cones are parallel to the optical axis.
This immediately restricts the diameter of the subject field to be no larger than the diameter of the front lens element, minus the diameter of the entrance cone at that point. The Raynox DCR 250 has glass about 35 mm diameter, so that's the absolute limit using that lens.
When you construct a telecentric combo by adding a positive achromat in front of another lens, then what's needed is to place the added achromat exactly its own focal length in front of the entrance pupil of the other lens.
With the Canon 100mm f/2.8 L and the Raynox DCR 250, one way that happens is when the lenses are mounted and focused as shown above.
However, the entrance pupil of the macro lens moves forward as the lens is focused toward infinity. If the Raynox is moved forward to stay one focal length in front, then the combo will remain telecentric while the magnification drops. The limiting case with the 100/2.8L focused at infinity is shown here, with about 44 mm extension between the lenses:
In this configuration, the combo has a magnification of 0.8, field width about 27.5 mm on my Canon T1i. Conveniently this makes the frame diagonal about 33.5 mm, almost perfectly matching the size limit imposed by the front element of the Raynox. Even more conveniently, image quality remains high clear to the corners. (Thank you for prompting me to check this configuration.)
So, on my Canon T1i, the answer is 0.8X for the question "how low in magnification can one go with this optical system?"
With other cameras and lenses, the same question would have other answers. I have no idea where the entrance pupil is for other lenses, and the fact that your full-frame camera will cover a wider field at the same magnification will also factor in.
If you want to play with this stuff, I suggest reviewing my thread on
Telecentric optics, third round. There's a lot of discussion there, and the setup
described by Ulf may bear directly on your question.
--Rik
Edit: For future reference, the adaptor stack in back of the Raynox is described by seta666 in
THIS thread.