Grok is from Robert A. Heinlein. I believe the first reference is Stranger in a Strange Land. He would probably be okay with billionaires, too. He was also a promoter of competence and critical thinking, so he might have held Elon specifically in disdain.

Inside the federation it's very very close to post scarcity but it's not quite perfect. Outside the federation like we see in the delta quadrant it's 100% not and a overall story line for like 4 seasons was them getting chased around with everyone trying to steal replicator technology.

I didn't watch Picard. How did Geordie end up with the Enterprise?

Various Star Fleet officers have periodically violated Federation rules and guidelines to achieve some ideological goal or moral imperative that cuts across the fleet's stated mission. Like with anything there's limits - Starfleet has its own police, crews can mutiny, eventually you run out of dilithium to gas up your warp drive so you can't go rogue forever. But for a deep space galaxy class vessel, they're regularly stuck making their own decisions under a military autocracy.

The Starfleet Admiralty Problem is a chronic plotline in the series, with admirals routinely engaged in all sorts of corrupt practices and villainous endeavors. Every captain from Kirk to Freeman has to deal with their share of higher ranking officers fucking around and being dumb assholes. Hell, Kirk himself is demoted from Admiral to Captain for going rogue in The Voyage Home.