I find following naming conventions to be stressful, especially the Apple names. I just name the files 20.png, 36.png, and so on. There could be a folder to choose, but that might still require editing the xml to point to the other folder.
The idea of having all the different icons is so that you could in theory give small screen users an easy to read icon, and bigger screen users could be given a fancier designed icon. In practice though I'm sure we all just resize the one icon. Some tools do that for you, you just give it one icon and it creates all the others for you. That would solve part of the problem, the AIR compiler would make Android sizes when building for Android and iOS sizes when building for iOS. But, we would still have to wait for AIR to be updated each time there are new icon size requirements.
Another issue is that iOS icons need to be square, the rounded corners are done by iOS. When I make the Android version I use a rounded corner version of the same icon, using the typical iOS 7 shape.
So, the easiest way I could see it working would be that in Flash you would select one icon file, 1024x1024 let's say, and click a checkbox if you want the corners to be rounded or not. AIR would then make all of the icons for you while it builds the app.
