Breakpoint that breaks when data changes in a managed language

What about swapping out List<T> for ObservableCollection<T> and listen for the CollectionChanged event? It implements the IList<T> interface so there should be enough overlap in available methods to result in syntax and semantic compatibility.

This is not possible in C# or any of the other .NET languages due to CLR limitations. The Visual Studio native code debugger supports data breakpoints (link) for C++ code which do exactly this but this is not supported for managed code. You could try to break on or intercept Add and Remove method calls on the collection as suggested in the other answer to this question.