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Honest question(not trolling, I swear):

Is it me, or is dealing with Stripe, or any HTTP API in javascript more of a pain in the ass, with it's asynchronous model and callbacks, than other languages? I much rather deal with and API in say...Ruby, than JS.

I think you might be right. Even with the old-fashioned PHP it is easier. I think the difficulty arises due to JS being more client-side focussed.
It definitely requires some additional work. They are both advantages as disadvantages with JS.