I don't think this is achievable with Shopping Cart Rules, particularly if you want your delivery costs to be separate to the product prices (from an accounting point of view you may want to keep track on delivery).
Hence...
...you need to write your own shipping module.
Here is the tutorial I have found to be of the most use:
http://www.excellencemagentoblog.com/magento-create-custom-shipping-method
Included in the tutorial are lots of examples of how to iterate over the cart and apply custom rules.
A module may seem a lot of work, however, once you have something you will be able to do a better job of shipping, for the customer, the company book keeper and the bottom line.