Firstly I strongly agree with everything you said and also just wanted to say this was a very eloquent description that i hope i remember a year from now.
I wanted to suggest a kind of alternative for discussion. I think there was something magical about the early web in that it offered a new way of interacting with the world that did not previously exist. It was difficult or impossible to find people that shared my interests (etc) before it, and usually that meant to just kept a large part of myself internal. I agree we have also changed, and there’s nostalgia involved, and that the internet does exist still the way we remember and even ion more ways we don’t appreciate but our kids will.
However i think there is also a bit of frustration that that initial burst of excitement did not continue to develop. When i read on HN and realize just how many people there are like me, or that there’s people that are also way too into disc golf, acoustic guitar, or any other semi niche activity i wonder why it is so hard to make more regular connections and interactions with them. Posting semi anonymously to HN with people i may never speak with again is a HUGE improvement over life before it, but it’s still a very limited experience. With facebook and reddit we have imho suboptimal platforms that have captured much of this magic and perhaps stunned their growth. I don’t mean to be pessimistic and the current internet is absolutely improved on uncountable ways from the one we remember. I suspect a bit of the frustration is some people’s inner belief that we could have something even better and somehow we are stuck.