So after a LOT of taping, we went to work and painted away.
Definitely adds some character to the house, and gives it more curb appeal. We are very happy with the way it turned out, and plan on painting all the windows of the house that way. Eventually, we will probably upgrade our windows and get new ones (that aren't as drafty). When we do that, we'll stick with the black sashes. We really love them!
I don't have a finished picture without all the tape off, but you get the idea. Once we finished painting them, we put the shutters back up and called it a day and a job well done.