jdohlinger,
Attached is a modified version of your posted workbook.
Because there could be a Tom Johnson that would get the discounts, I decided to check both the First and Last Name to make sure it is Tom Hanna. So, in J2 and copied down:
Then in K2 and copied down:=IF(OR(A2&B2="TomHanna",E2<I2),0,G2*H2*(1+(C2="T-Shirt")))
=G2-J2
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