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The functionality as you describe will have to be extended with custom programming. The configurable products act as a single product, so they won’t let you “drill down” to find a product. They just let you select your “options” for the single configurable product.
That’s odd. As far as I can see all the configurable product does is to allow you to drill down to the particular product you are interested in. I would like it to work as a single product with different options but it doesn’t. If you treat it as a single product, set up tier pricing and buy, say, 100 of them in different sizes and colour you should be eligible for the bulk discount you set up on the product earlier. But in fact what is added to the cart is several different products and you don’t get the discount. Maybe this is a bug then?