long-term active accounts can get hacked. I absolutely agree with support staff needing to provide more information, but they can't just blanket whitelist any old account
Did a ten year old account that does $1k a year suddenly bill $1M? Sure, flag that... but maybe give them a phone call, too.
Care for the customer can make or break a company. If stripe wanted big customers they can't be this careless
(and just to be fair to Stripe there seems to be a lot of customers as well that know crap about best financial/accounting/compliance practices and don't know why Stripe might have an issue with somethings)