Incredible article, a lot to unpack here, but I found this particular offhand tidbit interesting. It does seem like any attempt at tech industry regulation over the past decade or two (that isn't somewhat in the interests of big tech anyway, i.e. age verification and so on) has been either overly vague, or overly specific, leading to easy workarounds.
It seems like a microcosm of a wider trend in regulation; the disconnect between intentions and results. On the rare occasions that consumer-friendly legislation does go through, there is no working mechanism for evaluating its effectiveness and refining the rules as quickly as big corporations can adapt to them. I like how the article frames this, of how the regulations are targeting the wrong thing, how they're defined by the problem rather than the desired end state.
For more thoughts along these lines I'd highly recommend checking out Jennifer Pahlka's blog Eating Policy: https://www.eatingpolicy.com/