I hate being Debbie Downer in these threads, but the feasibility of a double shot, triple shot, or engraving is little to none (at least with that font).
Your best bet is Dye Sub.
Thanks, part of the point of me posting was to find out the feasibility of this design. Would a dye-sub be possible? I thought you can't use brighter colors on darker caps (so red and yellow I had assumed would not be an option for dye-sub on a black cap)
Yep, building on what i3 said, whichever way you go you're going to have to sacrifice at least one element of the design.
Triple-shots: essentially an impossibility right now
Double-shots: only two colours, and the font will have to change
Engraving: cannot choose colour of legend, font will have to change; you can go try ordering one from WASD now
Dye-sub: light-coloured legends cannot be printed onto darker coloured keys
Midair collision. Why would the font have to change for the double-shot? What aspect of this wouldn't work it? The sharpness of the lettering?
Also the reason I mentioned a laser-etched is because from what I understand the black keys are etched and then the etching is filled with white paint. It seemed like that would be the best bet for being able to achieve a more complex design like this. Similarly I am wondering though why the font would need to change?
Also I'd like to reiterate - thanks for your input, I am not yet an expert on keycap production although I do find the details interesting and am glad to be learning more from the more experienced members of this community.