See "Yesterday Is Tomorrow: Revisiting Annie as a new New Deal dawns," by Brian Doherty, Reason May 2009. IDW is doing an excellent job reprinting the strips. Gray's strip was one of the great adventure strips, but appeals particularly to Reason because, "The comic’s early days hold a winningly libertarian disdain for the uplifters and professional licensing and child labor laws that stymie Annie’s attempts to support herself and others who fall under her care."
As far as I know, the Reason guys are still hanging out on Dupont Circle.