Hey Michelle,

You could create a custom Umbraco data type that would have your categories and alternative pricing.

Then create an Extension method off of IProductContentBase (so it will work for products and variants) to override Merchello's price based on settings found in the datatype as you are adding the item to the basket.

Merchello does to a price validation check which you can either replace with your own custom version or simply comment out in the merchello.config

       <taskChain alias="ItemCacheValidation">
  <!-- Added Merchello Version 1.11.0
  This chain validates basket and wish list items against values in the back office to assert that the customer has not
  added items to their basket that were subsequently changed in the back office prior to checkout.  The process is needed
  as the relation between the basket and wish list items are decoupled from the actual persisted values.
  -->
    <tasks>
        <task type="Merchello.Web.Validation.Tasks.ValidateProductsExistTask, Merchello.Web" />
        <!--
            The following task is intended to assert that pricing and/or on sale value has not changed in the back office since the
            customer has placed an item into their basket or wish list. If you have made custom pricing modifications in your
            implementation, you may either remove this task or adjust your code to add a new extended data value
            merchLineItemAllowsValidation = false
            to the line item so that it is skipped in the validation process.
        -->
        <task type="Merchello.Web.Validation.Tasks.ValidateProductPriceTask, Merchello.Web" />
        <!--
            Validates that products are still in inventory
        -->
        <task type="Merchello.Web.Validation.Tasks.ValidateProductInventoryTask, Merchello.Web" />
    </tasks>
  </taskChain>

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