One more specialist I tend to think increasing head hit chance might be useful would be dagger specialist using special attack which bypasses armor. Yet again, daggers themselves doesn’t give bonus to hit the head so you wouldn’t get as much out of it as with flails.
Btw.: many if not all 1tile range 2H weapons hit both head and body during attack, so I ques increasing hit chance with them is pointless. Or?
Puncture cannot do critical damage (and doesn’t get bonus damage from double-grip either), so sadly a headhunter build won’t work for daggers.
As for hitting both body and head… Only axes do that as far as I know. And even then. If you get a headshot, 100% of the damage will be applied to the head. Only if you hit the body will it also hit the head. At least thats what I remember. I am not really using greataxes because their round swing is so awkward to use.