Hi everyone. I am developing a site selling apparel, and it operates out of Massachusetts. Unfortunately, Mass has some wacky rules regarding sales tax.

Basically, I need to collect sales tax based on product type and value. Apparel is generally not taxable, unless it sells for over $175. In that case, the tax basis is its price, less $175. (Ex: $250 jacket > $75 is taxable at 5%). This happens on a product by product basis (each product is taxed individually, not the value of the whole order). Of course, it also depends on what type of product it is (ex: jogging shoes exempt, golf shoes taxable).

I can use Workflow to find add a rule based on Shipping State, but what about the value issue? A couple things I am considering:

Add a checkbox field ("is_ma_taxable")
and/or
Add a custom field ("ma_tax_basis") - could this be calculated automatically using Tokens or some other way?
and/or
some Workflow logic based on taxonomy and categorization.

My concern is that I do this in a way that is both simple now, and easy to fix if MA changes its rules. Consequently, I would like to avoid doing anything on a product-by-product basis since I don't know of easy any way to make sweeping product changes in Uber.

I know its a complex question, but I am hoping that someone who has tackled this issue can offer an opinion. Thanks in advance!!