I currently have 2 windows in my storyboard. I am able to get one of the windows to show up by selecting it as the inital window. however i am not able to get both windows to pop up?
If you are wanting to have both up at the start, you could always create a named show segue from the first window to the second in storyboard, then in the viewDidLoad of the first window you can make the second window popup with:
self.performSegueWithIdentifier("SegueName", sender: self)