Help setting up Pricing Scheme for Wholesale/NonWholesale Customers

Hey everyone. So I have a somewhat challenging thing I'm trying to work out here. We've got two classes of customer - wholesale and retail. I've setup various price levels and price groups in the system as needed. We've also created a custom classification field on our items named Item Class that we use for organizing types of items within our store. (No relation to the system Class field).

Retail customers should pay base price on the items all the time, wholesale customers receive a certain percentage off base depending on the custom item class above. All of this currently works well - we setup a wholesale customer with group pricing so that when they do a transaction the items are marked down accordingly. We aren't concerned with quantity discounts here, just discounts on the custom item class.