How to Auto-generate Multiple Custom Columns in a WPF DataGrid for Same Type Properties

Auto-generating multiple custom columns in a WPF DataGrid in case where the data class has multiple properties of the same type doesn’t work like one would have expected because the custom control’s data context is not the property one intends to bind to, but the containing instance. So, the custom control or its view model doesn't know to which of the same-type properties to bind.