What we ended up with was a completely integrated rules solution that could be applied on a per user basis. It covered all the things related to products in WooCommerce (Variable, Variations, Simple, Attributes, Categories, Tags) and works on a prioritization method for logic flow.
It was also built with performance in mind for the customer. A number of the demographic sites have higher traffic loads and doing large and slow queries during page loads was simply not an option. Solution: a combination of custom tables that auto-update as things within WordPress/WooCommerce happen and a methodology of only run queries when you need to.
This top-down approach works well with or without caching and uses minimal code-level logic to prevent longer load times.