Ok figured it out with help from this question: How to map lists with ValueInjector
I needed to query the USERTABLE into a list and inject it like stated below:
Query:
Dim dataSubObject = (From ....).toList()
Injection:
Dim viewModel = New EventViewModel
viewModel.USERS= dataSubObject.Select(Function(x) New ImageViewModel().InjectFrom(x)).Cast(Of ImageViewModel)().ToList()