The line I always liked but is unusable in reality for sexual harassment reasons is the Seinfeld reference of telling someone who sneezed, "You are soooo good-looking".
This is just standard boilerplate language, and whether a particular product or company includes it or not is entirely a function of that company's legal department and has no bearing at all on the future behavior of the company.
That is to say, everything in here is true of everything, whether they tell you that or not, and literally zero information is gained from seeing it explicitly stated. If they'd completely left it out, it would still be true.
I will say, the internet in 1998 looked nothing like the internet today. There was barely any commerce at all. 1998 is maybe the year you'd start to say that Amazon "made it", but even then the common take from established reporters was that they'd never be able to compete with brick and mortar booksellers like Barnes and Noble. To the extent that the average person was even aware that you could buy things on the internet, it was mostly because they'd heard that it was dangerous to use your credit card online.
At the time, the web was still pretty small. Google launched in 1998 -- prior to that Yahoo was the most popular "search engine", but Yahoo was mostly a human-curated list of web pages organized by topic. Windows 95 was still what most people used, and it didn't even come with a TCP/IP stack enabled.
Certainly not a brilliant prediction, but it's hindsight that takes it from "pretty mediocre take" to "comically stupid".
As far as I'm aware, this isn't necessarily true.
The DMCA sets out several requirements for eligibility for the "safe harbor" provisions, but they basically boil down to "you can't be the entity that posts infringing material, and you need to remove infringing material when notified of the infringement" plus some legal stuff around having a designated agent to receive complaints, etc.
Having the moderators be Reddit themselves doesn't present a problem here. If Reddit themselves start actually uploading infringing material, then they'd have no protection against a complaint on that material, but that's it.
Consider Twitter, YouTube, etc. All of them do 1st party moderation of copyrighted material, and they haven't lost their protection there either.
I don't think it's a problem of not learning the lesson. The problem is that you can't succeed in making a social network if you ask anyone to pay in any way. You need it to be useful, which means you need everyone on it, and everyone won't be on it if it costs anything or is otherwise gated behind even the smallest of hurdles. So rich VCs come in and say, "here's $100,000,000 to go make this thing invaluable, and then I want my money back with a handsome profit". Everyone in the game always knows that the product is going to get shitty when it comes time to pay the piper. Being shitty is a side-effect of making money. The gamble is that it'll be so ingrained in people's life than they'll begrudging eat the shit to keep using it. They're looking for the elbow in the curve -- how shitty can it be before everyone abandons it. That spot of maximum shittiness isn't a mistake -- it's the target.