Overview: From the bundling step if the total stock value of the cart is < $500 prepaid as an option should not be allowed. The only exception to this is if the CurrentUser.Operator is <> ""
The only way that CurrentUser.Operator is set is if the session is for a Laddawn employee. Laddawn employees have the right to override the hard $500 limit for prepaid orders.
So, on the Bundling Step of Checkout - Change shipping information popup, Laddawn Pays Shipping.enabled = (Stock value of the order is > $500 OR CurrentUser.Operator <>"")
Everything else should continue to work the same way.