>> companies that were doing old stuff The Right Way, with lots of well-considered automation and high-quality backups and well-documented, repeatable, largely scripted configuration

Are there any examples of this? I’m coming up on 20 years into my career and i’ve genuinely never seen a large company that had their IT function ticking over sweetly. Every single one had aspirations and had some things nailed to a greater or lesser extent but none were “done”.

If anything, things are a LOT better today. The old mis-configured MS Exhange host hanging off the office DSL line is gone these days. The MD / CEO’s password is unlikely to be Password1 nowadays.