I'm truly intrigued and curious... my startup Gitpilot (http://gitpilot.com/) is trying to solve a similar problem. Was Wingman conceived from any inspiration of Gitpilot? Truly curious, especially because of the airplane naming scheme.
Wingman is a friend you take to the bar, not an airplane. But props on your app/startup - pretty damn slick UI.
A wingman is the other pilot flying a sortie with you, supporting you in a dangerous mission. The bar-cruising friend only wishes he could be that awesome.