Detail from 'Sunset Track,' by Gen Montreuil. Working image supplied by Brian Buckland

Gen Montreuil, a Canadian artist and skydiver, has a Kickstarter project to take her on a head-down painting journey. Not both at the same time, but she does incorporate striking head-down images into her work. Check it out:

Dreams That Soar
Kickstarter Project page

kickstarter