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I put a disc brake on a '72 XLCH with little problem. Took some bit of fabrication, though. It can be done with a later model disc setup as you write. Still requires some fabrication. I think you can Google and find a link to a step-by-step on the disc brake conversion.
I also did a jockey shift a couple different ways - one was using a left hand throttle and keeping the shift lever on the right (Indian did it this way), and the other used the brake crossover. The brake crossover isn't hard, but requires a little imagination and fabricating skills. I turned the shift lever up, shortened it to about 3 inches long, attached a rod using a heim joint, ran that rod back to the brake crossover (with many troublesome bends) and attached it using another heim joint, fabbed a jockey lever out of flatbar, and attached it to the other side of the brake crossover. I didn't like how it worked because the bends in the rod made it feel "mushy", and it was easy to miss a shift. I later put a Dick Allen collector exhaust on and that allowed a redesign of the crossover arm to get a more direct connection.







