I like matching headstocks when the fretboard is dark and/or when the headstock wood is plain looking. Light colors (whites, yellows, pale greens and blues) can also look good next to a maple fretboards. My birdseye and figured maple headstocks are non-matching. I like seeing the figuring more than I want it to match the body. I also had a gold BFR Bongo with an all rosewood neck and fretboard. The grain in the rosewood was gorgeous so EB glossed to headstock instead of painting it... the right choice IMO.
