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There's a somewhat hidden feature in Android Studio that allows one to deploy their application to multiple devices by CTRL-Selecting devices in the "Select Deployment Target" dialog.
This simply allows for deploying one's application to multiple devices. It does not allow debugging multiple devices. In fact you can only debug a single application at a time with Android Studio. This is partly due to a limitation of Instant Run being enabled.
There is a similar feature request out there which is CLOSED FIXED, https://bugzilla.xamarin.com/show_bug.cgi?id=39356 however based on https://bugzilla.xamarin.com/show_bug.cgi?id=39356#c14 I suspect this behavior does not exist in Visual Studio for Mac. Secondly this feature doesn't exist in Visual Studio either.
You can deploy to multiple devices in VS by simply putting all the csproj projects as Startup. The thing is I never got more than one Android simulator to work on the same computer. We don't have plans on supporting multiple devices for the _same_ startup project, though.