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I have one. Still cuts just like a new.

Yes, you creating the Cutline ,regmarks and barcode in Illustrator, and Cutting with the CuttingMaster Plugin. You can send the job to print with any Printer or any Rip. After Barcode created you need to send the cut layer to Cuttingmaster and hold it in queue. Cuttingmaster will be your barcode...

It is Futura .

could be Bitsumishi

Yes You can

Auttera and Cerebri Sans Bold

FlexiSign does not require Roland Driver. it sends the plot file directly to the port. Hard to find cutter which cannot be run with it. I have sent you my contact details if you need assistance.

Both USB-Parallel or Serial could work with OMEGA. The serial needs to be null modem. On the Cutter COMMAND need to be set to MODE2. Do not even think to download any Roland driver.

Flexi is the best option. no need to convert, just open SCV directly. You even can use CASFonts as well. Connecting Roland Cutters to any computer is easy. Keep it on mind, in Roland Serial port, not all the Handshake pins are connected. It could be resolved in Flexi or with a special Roland Cable.

try Anavio and Geometos

Sonic Cut Thru Heavy

looks like Times New Roman

Check if the carriage not loose. select the correct type of blade holder: tool2 for 09U or tool3-9 for 15U. The offset is 0. it does not mean 0mm it just the default.

Byington Bold and Schneidler Medium

I see this is an old post, but I need to tell you, any Cutter can Be used on Win10, Win7 or MacOS without any Virtual downgraded system. Specially Roland ones.

FlexiSign color search:

Nakser

Monoton Regular

Roycroft Regular, and Cobo Slab.

Roll 1 brings the material back to the end and set zero point there. Roll 2 keeps the zero point where you filled in. If the head position is just before the barcode it should scan it, but if it is after, it won't go back to search it, because it is behind the zero point.