I generally prefer matching headstocks with solid colors (transluscent or otherwise), and plain headstocks with 'bursts and sparkle colors. But whether a guitar had a matching headstock or not wouldn't really be a consideration in my decision to buy it in the end...
I generally dislike Fenders with painted headstocks, but like how they look on EBMMs - adds a nice touch of class. esp. if the color is a translucent or burst.
That said, I still like the plain vanilla ones on EBMMs equally as much too - especially so if they're covered with a nice dusting of birdseyes (and/or flame)!