Rob, I wanted to let you know that in Dave Byrd's new book, on page 50 there is shown rifling equipment from the McInturff gun shop. One of the two guides shown is of similar design to yours. It however is obviously a gain twist guide; as the fast part of the spiral is near the handle, the barrel when mounted in the bench would have to have been with the breech closest to the guide and the muzzle pointed away from the guide.
The head block with the three guide teeth is the one that goes to this guide. the handled thin rod appears to be for pushing a float, either to frisch or lap; the very bottom "rod" appears to be the remains of either a drill or a reamer, but the picture is not clear enough to tell which.
P.S. Thanks again to Mr. Byrd for a significant step forward in documenting the Tennessee long rifle with his new book.