"So im guessing the method you mentioned wouldnt work for that"
you could crate another record in the settings table for the second items shipping. Add another recordset to retrieve it, and add another set session value behavior
"if i am planning on using shipping cost as a item per item then why wouldnt it be a fixed shipping cost value"
because a flat rate wouldn't take into account the items in the cart and the shipping amount to apply to them, it's just that: a flat rat. regardless of what is in the cart it is the same rate.
for per item shipping, you would store the shipping rate in a cart column, then you could do a multiple of column subtotal calculation to use the subtotal of the shipping rate column.
