I've worked in a lot of industries from heavily-regulated healthcare, financial, core developer tooling, and a lot of YC startups. It always pays off in the end to consider code primarily for engineers, and every time I see people take those kinds of shortcuts in non-bet-the-company situations, they regret it. Especially in situations where you're handling large flows of cash or data, a percentage point can sink your entire business. Certainly a HIPAA violation can add zeros quickly.

I've actually been doing a lot of turnaround consulting with companies that took a short term mindset, got stuck, and had to step back and revamp their technical processes like you say. It's always more expensive to redo it after the fact, but I'm happy to take their money and fix their mistakes.

And that's not to say that it's not a tradeoff, but it's about being conscious of the tradeoffs involved and making reasonable choices.