I have to do Command+Enter multiple times so that the app can be deployed and run on any iOS emulator. The deployment fails and with each attempt it progresses and finally deploys and runs. That appears to be some timeout issue.
Once the app is loaded to the emulator, it can be run even without the debugger attached.
I have XS 5.5.2, Xamarin.IOS 184.108.40.206, Xcode 6.0.1 and my MBP (mid 2010 mode) is running OS X 10.9.5.
Does anyone else have similar issue? Any workaround?