I can't comment about the webhooks thing more than to say I think its possible.
I would also like to do a better Stripe integration into Aware (I have the Stripe plugin we collectively develloped a couple of years ago but doesn't work due to the storing locally of CC information i.e unusable for me) so following this + wondering if anyone else done this?
Rocketman, you write Stripe advise against the API approach? Why and what do they recommend instead?