Unfortunately, currently we do not have such an example that demonstrates how to achieve the desired by you exact behavior with ObservableCollection. As you have already noticed in order to perform the desired filtering the CollectionViewSource needs to be used, but that will cause the initial observed selection issue. The only approach that we could think of in order to continue using the ObservableCollection and achieve the desired behavior is to remove the item from collection when the button gets pressed and add it to the collection that corresponds to the changed category.
I hope this will help you.
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