To a point, yes. I mean, bikes have changed a ton in 51 years and I guarantee you my dad would struggle to work on the newfangled high end high tech stuff, nor would he be the guy that you'd want to professionally fit you to your new road bike. He's got people on the payroll who do that, for sure.

Bookkeeping is different, though. He's actually been defrauded by a bookkeeper in the early 1980s. I don't know the details but she was siphoning money from the business in some scheme, probably a 1981 version of OP's Stripe API issue. If you simply trust a person like this and don't verify regularly, the mistakes and frauds happen. Receipts is where the rubber meets the road for a retail biz and I just don't see a substitute for an owner who cares and checks.