It's not that hard, but you'll need to take off the caliper. It's gonna be tough as hell to do on the car.
The CObra caliper I did with VHT spray caliper paint. I did a few coats in red, let it dry and then used a small brush to paint the COBRA in black. Other guys tape the COBRA lettering very carefully and then paint the caliper and peel the paint off.
The Mach 1 calipers i did using the Duplicolor brush on paint. It worked pretty well and was easy since the Mach 1 caliper lacks any wording.