Possible.
Flexrip T4 will give you the 1-bit TIFF screened separations, you must choose a resolution supported on the imagesetter for output. However, EskoArtwork can not drive the Hercules directly.
If you do have the interface that comes with that imagesetter and it will accept the TIFF's then you are golden. If you do not have the interface, then try looking at a Raster Blaster (they support Hercules) and ask for a 1-bit TIFF catcher.