Matching headstocks are the correct choice on any solid/metallic/flake/candy etc finish (and natural, obviously). At least, on RW/IL/Ebony. For bacon it's kind of a mixed bag mostly because I hate bacon fretboards. On Maple - it's USUALLY a yes, but not as consistently as dark boards.
Tuxedo maple Tele's are an example exception to that. As for bursts - it's REALLY dependent on the guitar. On masterpieces like my Stardust Elite:
Unambiguous. That burst had to match. On a 3-tone strat? Please, please no.