Problem 1) My client want to run a special promotion where he gives away a product, but charges shipping. He doesn't care how many times they order this small product, as long as they pay shipping, then he breaks even. Currently the shipping is a table rate. Somehow I need to make a this so that it always has a per item shipping charge, yet if they order a regular product the shipping still remains at the table rate.

The only solution I can come up with is to make a separate product listing for this item, limit quantity to 1, and price it at 0.0. Does anyone know a better way to achieve my goal?

Problem 2) My client has 1 item that is oversized, he wants to add 20.00 to the shipping on this item, the cost makes the item go into free shippping on the table rate. Is there some way other than adding it to the base cost of the item and advertising it in the description?

Maybe I just need a new client?