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(http://i.imgur.com/eIEi9s6.png)
Given that the current ducky caps use "water transfer printing" on their backlit caps to paint them, I think it would be very difficult to do an at-home paint job of backlit caps. Legends need to be very precise ><
That's the biggest problem. Preserving the legends on a backlit set. But I'm sure most people are tired of boring old black and white backlit keycaps.
One alternative is watercolor with acrylic layer on top. Watercolor is translucent. In fact if using watercolor, I will probably risk my Deck keycaps.