I guess I need to cross one bridge at a time. I followed the instructions for the first rule and tested and I just got error messages. Just so I'm clear here is what I have and what I need for the first part.
My Products database is pretty basic productid, productname, productprice, etc and I added a field called shipping. Each product will have it's shipping determined by that product database field.
Product1 cost $5 to ship
Product2 cost $10 to ship
A client buys 2 Product1 and 1 Product2
On checkout the calculation is:
Total shipping would be ($5+$5)+($10)=$20