After more digging we've found that the issue is the call to -[NSWindow setStyleMask:]. It does not result in an event propagating properly.

After more digging it turns out that the NSViewFrameDidChangeNotification event fires properly. The issue is that the system disassociates the view from the window for a while, so when the event handler is called then there it cannot find the associated window. I confirmed this by overloading -[NSView viewDidMoveToWindow].

The fix is either to have a way of finding the associated window without using -[NSView window], or making sure to sync up things when we get reassigned to a window. I think the latter is safer as I'm not sure how safe it is to manipulate the view when it isn't properly associated with it's window.

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