> I got pressure from the CEO saying it wasn't reliable to host our own infrastructure anymore even though our total internal down time over the last 5 years is significantly less than even a single of the larger recent AWS outages.

Same here. My job as a software dev does not require me to self-host services we need and use. Quite the opposite. But, I am reluctant to hand over all control to AWS or equivalent for several reasons that I will get into here.

I have found that Infrastructure as Code (IaC) and modern tools like opentofu, ansible, combined with frontier AI models and harnesses gives you superpowers in this space. Almost all of our self-hosted services are fully managed by these tools. e.g. We perform backups and test them more often now than we ever did before. Entirely because it is so much easier to do all of that now.