Fact is, we think things are getting more simple, but they aren't. There are things that come and go. for example I think there are aspects of social media that have come and gone for certain companies. So things abandoned mean, less tech, but if anything, products and services are becoming more integrated and that's not making it easier requiring less intervention. And that comes from the drive within a company to progress in some form. Some of it is the drive for higher numbers. Some of the drive is to take on or improve the creation process or value-adds for customers.
I think certain people who grew up with Star Trek always have a strange impression of what tech debt and tech maintenance is. As if a team of 10 or 12 on a Starship of a thousand people is enough to maintain all those systems including the propulsion hardware, medical facilities. You can crawl around in those clean hallways, point a diagnostic probe at a part of the system, maybe pull out a chip and reseat or replace... then all done! Yah right.
More and more devices with potential connectivity, and more software and entertainment and facilities and service provisioning. IT is not going away. I'm not sure what peak IT looks like but we're not really close or going to see a downward slope just because Cringely feels like he needs less in HIS life and is getting long in the tooth and simply doesn't foresee where things can go.