Draw it up on Tracing paper over the top of your Paddle Headstock, you can overlay other sheets of tracing paper and make tweaks to the base design to see what you think.
If you had a 4-5mm radius on those corners and then ran your curve between them it would look pretty schmick I think. You could also look at turning that curve into a bevel, to avoid any string clearance issues. But that might not play well with your pointy design cues.