I believe I understand the issues. Please keep in mind that one of the problems I mentioned nine days ago in my first reply on this thread was that interpolated curves were “rounding the corners” in the process of lifting the tool at the end of each path (stroke). Which is why I removed the vertical entry and exit lines from the font creation clusters.
I may have more to say on this subject later but for now, would like you to look at this 5-axis CNC project I contributed to five years ago on this forum. You can download the GH file and play with it when you have access to Rhino:
Or look at this short video I just made of it:
I am not an expert on calligraphy or robots by any means, but enjoy geometry and have some talent at programming. Yes, it would be fun “to work with you hands on in the lab” but that isn’t likely, and me buying a robot isn’t either. So exchanging forum posts and GH code might be all we can do. As the I Ching says, “perseverance furthers”.