[MuffinFlavored]

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.?

[ceejayoz]

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...