There's quite a bit more complexity in some use cases. Some payments are now asynchronous due to https://en.wikipedia.org/wiki/Strong_customer_authentication ; handling failed payments for things like subscriptions takes some effort (and managing webhooks).
My experience with Stripe has been great, but payments can still get into the weeds through no fault of Stripe's.
Some other examples of complex use cases: connected accounts, reconciliation reports, dunning reports, non-traditional ecommerce workflows. From a security perspective, I'd love the ability to enforce 2FA instead of having to audit the users table every month. To be fair I think the number of clients with 50+ connected accounts is fairly low
I might sound a bit dumb here, but would a cron job that runs daily, finds customers who haven't been billed in 30 days, then tries to bill them and disables their account on failure easier than dealing with webhooks/etc.?
Potentially, but Stripe has a lot of features you might have to duplicate in that case. They automatically re-attempt (including machine learning that tries to do it when the card's least likely to be maxed out). They send email receipts, handle SCA notifications if additional authentication is required...
My experience with Stripe has been great, but payments can still get into the weeds through no fault of Stripe's.