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Here is how I have it broken down. For shippable items there are three categories USPS Small, Medium and Large then for non-shippable items there is local pickup and delivery. The conditions for non-shippable was easy to do since its just a condition by state which is easy to do. For shippable I have added a field to products with taxonomy terms shipping small, shipping medium and shipping large which this way I can set up what kind of shipping I want for that item when I am setting it up. Now I've tried just about everything to set a condition for the small items set up in products to work with just the usps small flat rate I set up. I am going to add calculations per item after this is set up but there is already a video tutorial on how to do that.