I have been making a plane in blender for some time now and the one thing I cannot get around is adding thickness to windows on a plane. I have been making the plane using a cylinder and are NOT going to use sub surf to add a smoothing effect. Instead I am using the shade as smooth option. I am using the solidify modifier to add the thickness to the windows and then using boolean to cut out the shapes of the window. I have good sources that tell me it is possible to use boolean and still get good results. One the boolean as applied it completely messes up the surface of the cylinder. I have one refrence image as to what I would like the end result to be like.