1) CDA section 230 was written before the phrase "social media" was invented, when the Internet barely existed, and many people were still on AOL, Compuserve, and Prodigy.
2) Section 230 was, in fact, intended for exactly the opposite purpose. It was written because previous court rulings indicated that moderating could make you more liable, and legislators realized that was precisely the opposite of what they wanted to encourage ("nobody would have any incentive to keep the internet civil"), so they wrote section 230 to make sure that sites weren't liable if they moderate but don't catch everything.
Read https://en.wikipedia.org/wiki/Section_230_of_the_Communicati... for details.
Yes, he is. He is telling the FCC, etc., to issue regulations “clarifying” section 230; regulations clarifying law exist specifically to guide the courts in application, and courts grant such regulations (where properly authorized under statute) great deference, which Trump clearly hopes to benefit from.
“Clarifying” regulation specifically is a message to the courts on interpretation; directing executive agencies to craft clarifying regulation is directing subordinate executive officers to tell the courts.
Correct but irrelevant.
I can tell people things over whom I don't have directive authority. “Clarifying” regulations are exactly the executive telling the courts how the law should be interpreted.
Courts can disregard them (and, in principle, will if they don't find them the issuing agency to have been empowered to enforce the law and thereby entrusted with that interpretive role, and even if they are authorized, they deference granted to them is not unlimited) but the fact that someone might not follow your direction to them doesn't mean you haven't given them direction.
EOs tell the EXECUTIVE BRANCH how to enforce laws.
They do not tell the courts how to interpret them.
Yes, EOs tell executive branch officers what to do.
One of the things this EO tells certain executive branch officers to do is to tell the courts how to interpret Section 230 by way of adopting “clarifying” regulations.
Courts ignore executive orders - especially ones from republican presidents, essentially always.