Separating entitlements from SKUs makes a lot of sense and definitely saves a lot of engineering edge case nightmares around renewals. It also gets super messy

Separating entitlements from SKUs makes a lot of sense and definitely saves a lot of engineering edge case nightmares around renewals. It also gets super messy after a couple years of pricing iterations. Eventually your plan distribution doesn’t reflect feature access which doesn’t necessarily reflect feature usage. Future changes to optimize packaging only have limited impact because it’s so hard to tie back who has each entitlement and why. IMO it’s super important to document the WHY every time a customer’s entitlements are separated from their plan (especially if an account mgr will ever be involved in a renewal). Also periodically undoing extra unused entitlements helps to keeping things clean.