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That’s ambitious, but entirely unrealistic in many cases.

For one thing, people do screenshot/download/archive web sites; these copies don’t get updated, and it can be important to know when they were last updated (as opposed to when the snapshot was created by a third party).

In that case he should put a "last updated" on each posts. Plus that would offer even more incentive to keep things up to date, since you're giving yourself a public "mark of shame" if you don't

It's extremely annoying because his posts get reposted to social media a lot and you suddenly have to go on a treasure hunt to figure out if he's revisiting old topics, or you read it five years ago.