Since this is an issue on the edge between Context and Pathauto, I'm going to submit it to both projects. It's difficult to me to judge which party should be more responsible for implementing the feature. Hopefully you guy can come to some agreement.

My case incorporates a product catalog. Since it is a subject to a fast grow, I want to make it as much scalable as possible.
A product is bound to a content type which has two taxonomy reference fields:
Taxonomy A specifies how the product is built, it is a single value ref field.
Taxonomy B specifies where the product can be used, and it is a multiple value field.
User can reach a given product by browsing either taxonomy.
The path (and breadcrumb as well) can look differently depending on from where user came from, but eventually should point to the same content node.
For instance:

domain.com/tax-a/branch1/branch2/branch3/product1
domain.com/tax-b/branch1/branch7/branch8/branch9/product1
domain.com/tax-b/branch1/branch7/branch11/product1
domain.com/tax-b/branch10/product1

I don't seem to be able to contextually define patterns. I would imagine to be able to define a pattern like:

[current-context-taxonomy-path]/[product-sku]

This would probably require to expand the UI options for Taxonomy Vocabularies, Context and Pathauto Tokens, but would seem to be most scalable solution possible. Since I'm quite fresh to Drupal, I could probably have overlooked some caveats in the logic, but I hope you can figure out my needs and find them reasonable for addressing in future releases.

Please let me know if you find it can be done with current versions of your excellent modules.
Thank you.