

To quote your quote:
I got the product launched. It worked. I was proud of what I’d created. Then came the moment that validated every concern in that MIT study: I needed to make a small change and realized I wasn’t confident I could do it. My own product, built under my direction, and I’d lost confidence in my ability to modify it.
I think the author just independently rediscovered “middle management”. Indeed, when you delegate the gruntwork under your responsibility, those same people are who you go to when addressing bugs and new requirements. It’s not on you to effect repairs: it’s on your team. I am Jack’s complete lack of surprise. The idea that relying on AI to do nuanced work like this and arrive at the exact correct answer to the problem, is naive at best. I’d be sweating too.

I’m going to call it like I saw it, a very long time ago.
<rant>
You have a product that is basically purpose built to make data hoarding and piracy practical, yet it requires a login with a central service. I don’t care what justification anyone thinks makes that worthwhile or even a good compromise. Signaling to any corporate entity that you’re in possession of such a thing is a bad idea to begin with. They shouldn’t even know you exist. That information, along with anything else you do with the product is compromising to you and can be sold for money if aggregated with everyone else’s data.
If you find this rant out of place in our modern world, I’d like to point to the concept of shifting baselines. This didn’t used to be normal and nothing short of greed continues the behavior. The technology before this ran/runs without anyone knowing. Consider VLC, or XBMC.