An enjoyable read! I get the sentiment and especially the frustration 100% but I'm definitely more pro-update. For one thing, it's generally less painful to perform gapless updates than it is to update from something that's multiple years and multiple major versions behind. Also as a developer I of course always want everyone to have auto-update turned on all the time to avoid the cost of legacy support that was outlined well in the article.
That said, I think the biggest underlying issue was kind of buried a bit: The Oracle vendor lock-in. Even more important than update policy is staying away from licensing agreements that can put you in a situation like that. Also that Docker screenshot was all kinds of WTF. Made me really glad I've stayed away from them as well.