Ok, so we were able to reproduce some of this today here at the office. In our case, we enabled sync over Wifi and then launched the editor. The device showed up in the editor on the Mac and when we tried to deploy to it we got the failure. Do you have Sync over Wifi enabled for the iPad? What about the iPhone 6+? If you have it enabled, can you try disabling it and then see if the deploy works correctly?
-Pete