This may have something to do with the issue you are having:
Roland CX and CM cutters need to be set to Rotate 90, and GX cutters need to be set to Rotate 0 to work in Flexi 8.5 and above (actually the 0 offset will show on the left edge of the Cut/Plot dialog). Prior releases, like yours, did not utilize this.
To change the rotation on the Roland GX machines...
- load media into the cutter
- press menu 2x's to show UNSETUP on the LCD
- press down arrow once to display CONDITION
- press right arrow to show FORCE
- press down arrow 4x's to show ROTATE _deg (where _ is either 0 or 90)
- press right arrow then down arrow to change to opposite value
- press enter to set then MENU 3x's to return to the first screen
- Turn off and on cutter
The origin should change to the opposite side.