Does subscription evaluation work solely depend on Asset?

Summary:

Customer can have contract for the same asset through different customer accounts.

Customer is expecting bill-to and ship-to customer account and site to be evaluated for application of the subscription.

Currently, if I create two subscriptions for the same asset and ship-to customer, but different bill-tos both gets apply on the debrief. Is this expected behavior regardless of bill-to customer?

User case:
For variety of factors sometimes, the same asset is serviced through different bill-to (customer resource, vendors, etc.). When debrief is created it will have appropriate ship-to and bill-to on it. Customer needs to be able to apply contracted price with bill-to for that asset.