I don't know anything about CAM, but maybe I can lighten up things a bit. As you describe your problem it seems to me that the cutting device is adressed as a printer, using the device's drivers installed in the OS, and printing out of the CAD program, as if printing on paper. Is this right?
In LibreCAD you have to set the paper size (probably equivalent to the engraving field size) at Options - Current Drawing Preferences - Paper.
When printing go to Print Preview mode. Set the scale, probably 1:1 in your case, and move the white paper sheet to the right position under the drawing. If this is not properly set the drawing might be outside of the sheet, so also outside of the cutting area resulting in "The Printed document contains no data." Maybe this is where your problem lies. You might test on a paper printer first.
Regarding Draftsight old and new, maybe new DS is very different.
Edit:Stay in Print Preview mode when printing.