Getting into LiveCode for iOS? Ask your questions here.
I can confirm that you need to start the iOS device in the Simulator first. I spent hours frustrated by the inability of LC to get the iOS Simulator to work (it kept timing out), only to discover later than I had to FIRST start a particular device (e.g. iPhone 6s) in the Simulator, then LC would transmit the app to it.
MacOS 10.14 Mojave, Windows OS 10, iOS 12.2, iPhone 5s and 6s, Android 7.0. Also programming in C and Java, and several other languages.