Well, the real question is "why headstock?". The important part of the string is between bridge and nut. Every string piece and mechanical part in
addition is unnecessary and might have disadvantages. Removing the headstock effects:
I build my own headless-hardware with main focus on these points. Well actually the most important thing is:
" The less friction you have in your guitar (swinging system) the more energy you can transform in acoustic vibration resulting in more sustain and consistency of sound.
Headless guitars are becoming more common for this. The rare "weird" look of the guitar might be a reason for a lot of people to look away. I think this is something you might come around with. Therefore you have a well balanced guitar with alot of benefits on tone and handling.