My latest blog entry, "Ordering Art for Games" is over at MonteCookGames.com, where I describe the process from a game designer POV. In addition to one of first art requests I ever made, way back in 1995, I also give a look behind the scenes for The Strange corebook we're getting in art for as I type this!
http://www.montecookgames.com/ordering-art-for-games/