Fulfillment vs Checkout webhook

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Hi there, I am trying to make a proof of concept app that interacts with a client's store. The app has a subscription to an event through webhook and validates the "shipping address" via a third-party (carrier) API endpoint to see if the address is deliverable.

1) Does webhook works in the storefront as it is an "AdminAPI"?

2) I want to check and prompt the user on the shipping page if the entered address is not deliverable before proceeding to payment. What is the best webhook I should subscribe to? Fulfillment or Checkout? What are the differences, when each of these webhook starts to notify?

3) Is it possible to send an abort/to cancel checkout API (DELETE) to the store if the address is not deliverable?

Thank you.