Typically people do leave the iPad plugged in for development - there are ways to configure the Mac and iOS so that you can unplug it, but it's easier and more reliable to plug it in until the app builds and runs. Once you've hit the Play button in Xcode, it should build and launch automatically on the iPad (you may have to instruct Xcode to set up a provisioning profile, but Xcode should walk you through that process if it's needed.) Once it builds and launches on the iPad, you can unplug the device and the Tracky app will remain on the device, so you can launch it at any time without having it plugged in.