I have thought about this quite a bit in the past. I feel we already have an implicit system in place for judging modern-weird based on retro-weird. For eg. This community and its kindred communities like VCs are judged based on the level of straussian takes(retro-wierd). Same goes with the Feynman movement, where everyone who has read(or has an idea of) “Surely you’re joking” starts generously distributing weirdness points to anyone who seems even mildly eccentric. Some examples of this are people like Eric Weinstein, his petty neologisms and vacuous abbreviations, but many people seem to like it because of his weirdness. This is to say that though I am not a fan of it, such a system is already in place and most of the elite institutions(companies, colleges etc) corroborate this by selecting for people with high weirdness quotient.
To me the downside of this is clear with the rise of movements like stoicism i.e., when you try to select for weirdness, the incentive forces many to try and act weird — not sustainable. Those who get exhausted trying will revert to the crutch of normalcy like stoicism which then becomes the mainstream. You can see this with the rising levels of anxiety and depression with online content creators trying to be unique/weird. Any system that filters unproductive Jerrys(Rick and Morty ref), in this case unweird Jerrys, will inevitably face the wrath of unweird Jerry army, thus nullifying the effort.