"But my pragmatism complicates itself at this moment?"
I would not call it pragmatism. I would call it a fear of change; staying in your comfort zone. Life is actually much simpler if you abandon your old way of thinking and adopt a new one (and I know exactly what you mean - I was in the same boat as you with the code).
Now, from my soap box and to a more practical answer:
If you want to detect changes in your model, pin events that will allow you to detect changes in your model. The DataContext is not really a model ... All of your model objects will have an INotifyPropertyChanged implementation. You must either connect to this for this model, or connect to something similar for the ObservableCollection.
Silverlight / WPF makes all of these things easier than data binding now works.
Do not fight with the frame. Do not bring the old ASP.Net methods with you to this game ... This will not help you. This way you lose the best parts of the frame.
Greetings.
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