To launch a simulator with a specific device booted I´m using list devices subcommand to get the list of all devices available
$ xcrun simctl list devices
== Devices ==
-- iOS 11.2 --
iPhone 5s (E3B6EA43-C805-49C2-9502-A44A465D8DF2) (Shutdown)
iPhone 6 (801E9E11-CA86-473A-9879-4B0742B827FB) (Shutdown)
iPhone 6 Plus (24013349-1A6F-489C-9A68-ABB00EBB4BBF) (Shutdown)
iPhone 6s (1A594D75-146C-4BEA-A250-1FADE7886114) (Shutdown)
iPhone 6s Plus (C2730FA0-11CB-49C9-A087-CB3C1BF1CC3D) (Shutdown)
iPhone 7 (F58B3749-3276-49E5-81C8-EBA1AEA7B242) (Shutdown)
iPhone 7 Plus (98167D8C-8F27-404C-AB02-588D9AAFD071) (Shutdown)
iPhone 8 (96322368-F763-4E0A-8576-ADE9F678211F) (Shutdown)
iPhone 8 Plus (E916D1EE-B67B-4C01-B3F5-C5C80CC4CDF8) (Shutdown)
iPhone SE (ABEFEDDF-7A7C-4B94-9E91-E065170FA47F) (Shutdown)
iPhone X (84DAB7AB-3CA2-4F5B-8C4E-A5B54CA15C31) (Shutdown)
iPad Air (DCD8CF4B-2C9F-4BA1-952A-ACB9CAD0A84D) (Shutdown)
iPad Air 2 (A47C9A05-233F-450F-9A39-318258E9ADEA) (Shutdown)
iPad (5th generation) (819C058E-64AC-4E73-8F41-2C0F919F8B56) (Booted)
this command will output a list of available devices with its UDIDs and statuses
Then I launch the simulator app specifying a device with the -CurrentDeviceUDID option
/Applications/Xcode.app/Contents/Developer/Applications/Simulator.app/Contents/MacOS/Simulator -CurrentDeviceUDID <DEVICE-UDID>
NOTE: replace the with a valid UDID from the list.
For example, if we want to launch the simulator with an Ipad (% generation booted):
/Applications/Xcode.app/Contents/Developer/Applications/Simulator.app/Contents/MacOS/Simulator -CurrentDeviceUDID 84DAB7AB-3CA2-4F5B-8C4E-A5B54CA15C31
UPDATE 23/05/2018
With Xcode 9.3 CurrentDevice UDID option is not working for me, as a workaround, I have to use simctl to boot the device in the simulator before open it.
xcrun simctl boot 2BF01FC0-7E29-4AF1-ADD1-886DF129A9A9
open -a Simulator
You can create, erase, delete, boot, shutdown and upgrade simulators using simctl.
$ xcrun simctl create
Usage: simctl create <name> <device type id> <runtime id>
$ xcrun simctl delete
Usage: simctl delete <device> [... <device n>] | unavailable
To get the list of valid device types and runtimes
xcrun simctl list devicetypes
xcrun simctl list runtimes