In order to do this effectively you need to use calculations with your shipping rules. First add three calculations:
1) PistolCaseQty = ([ItemCatName]=='Pistol Carry Case')?[Quantity]:0
2) EliteCaseQty = ([ItemCatName]=='Elite Series Cases')?[Quantity]:0
3) StandardQty = ([ItemCatName]=='Elite Series Cases' || [ItemCatName]=='Pistol Carry Case')?0:[Quantity]
Then creating the rules becomes much easier:
1) Shipping & Handling : Trigger = SubTotal of StandardQty > 0 : Calculation = Flat rate $9.50
2) Shipping & Handling per item : Trigger = SubTotal of StandardQty > 1 : Calculation = Based on column subtotal StandardQty times 1
3) Pistol Case Shipping : Trigger = SubTotal of PistolCaseQty > 1 : Calculation = Based on column subtotal PistolCaseQty times 12.50
4) Elite Shipping : Trigger = SubTotal of EliteCaseQty > 1 : Calculation = Based on column subtotal EliteCaseQty times 12.50
