Java – Why would our Java app not display windows on secondary monitor

It violates encapsulation. You shouldn't be able to bypass the parent class's behaviour. It makes sense to sometimes be able to bypass your own class's behaviour (particularly from within the same method) but not your parent's. For example, suppose we have a base "collection of items", a subclass representing "a collection of red items" and a subclass of that representing "a collection of big red items". It makes sense to have:

public class Items
{
    public void add(Item item) { ... }
}

public class RedItems extends Items
{
    @Override
    public void add(Item item)
    {
        if (!item.isRed())
        {
            throw new NotRedItemException();
        }
        super.add(item);
    }
}

public class BigRedItems extends RedItems
{
    @Override
    public void add(Item item)
    {
        if (!item.isBig())
        {
            throw new NotBigItemException();
        }
        super.add(item);
    }
}

That's fine - RedItems can always be confident that the items it contains are all red. Now suppose we were able to call super.super.add():

public class NaughtyItems extends RedItems
{
    @Override
    public void add(Item item)
    {
        // I don't care if it's red or not. Take that, RedItems!
        super.super.add(item);
    }
}

Now we could add whatever we like, and the invariant in RedItems is broken.

Does that make sense?

No, a List<Dog> is not a List<Animal>. Consider what you can do with a List<Animal> - you can add any animal to it... including a cat. Now, can you logically add a cat to a litter of puppies? Absolutely not.

// Illegal code - because otherwise life would be Bad
List<Dog> dogs = new ArrayList<Dog>(); // ArrayList implements List
List<Animal> animals = dogs; // Awooga awooga
animals.add(new Cat());
Dog dog = dogs.get(0); // This should be safe, right?

Suddenly you have a very confused cat.

Now, you can't add a Cat to a List<? extends Animal> because you don't know it's a List<Cat>. You can retrieve a value and know that it will be an Animal, but you can't add arbitrary animals. The reverse is true for List<? super Animal> - in that case you can add an Animal to it safely, but you don't know anything about what might be retrieved from it, because it could be a List<Object>.