Do you think society is getting less equipped to maintain the complex machinery that it ultimately relies on?

Off the top of my head, a The first test of a society’s ability to maintain complex machinery that I can think of is the proper construction & maintenance of high-tension power lines, or Transmission lines.

To my knowledge, a safety factor (FoS) of “1” means that a Transmission line could stand up to the conditions of the worst storm to have occurred in the last 100 years. A (FoS) of 2, would withstand double the conditions of the worst storm. Transmission lines supposed to be designed to an FoS of 4

Maria was the 2nd worst storm to hit Puerto Rico in the last 100 years - the worst was in 1928.

Hurricane Maria sliced straight through these vital connections, only 15 percent of which were designed to withstand a Category 4 hurricane.

Is society less equipped to maintain its complex machinery?

I’m not sure, but Puerto Rico was never equipped in the first place.