To address your points:

* My friend is not a rockstar programmer. He's about average, and in San Francisco he was living in Bayview and getting his house and his car regularly broken into and barely scraping by. Now he lives like he makes 5x the money he did in SF and his taxes are vastly lower since he's making less money, but living better. This is one of the largest mysteries of modern capitalism. Why are the prices for things so vastly different in different countries?

* If the robots can run the futures market and do general purpose programming then we probably won't even need money because we will have perfected central planning. Instead the robots will be playing a game called "The Humans" which is like when we play "The Sims" with the goal of trying to make the Humans happy. This will go on at a superhuman level of intellect and we won't even be able to analyze what the heck is going on, much like we can't really know why Alpha Go makes the moves it makes. We just won't turn it off because we can't live without it. This is the good or bad future depending on the ultimate fitness function, which in the good future is make everybody happy and not where the fitness future is based on deep ecology (DE) [1] which would prefer a 95% population reduction.

* My friend might not be a web developer, but he could probably get a job working on designing some guy's Burning Man float who owned a robot for enough to live well since it would require an absolutely trivial amount of effort to live since there would be so much supply.

* As far as Libertarianism goes, your formulation seems to be that that means no rules. No not really. I don't think ANY libertarian that is respected by the libertarian community would think slavery or poisoning people should be legal so you really have got a strawman there. Besides if we had no rules at all the wealthy Deep Ecology people could get together and decide they wanted to exterminate everybody they don't need to maintain things with killer robots who unlike in the movies have perfect aim and tactical strategy.

* The foreclosures during the great depression were due to collapse of bank reserves due to fractional reserve banking. You had short panics in the 19th century before the fed and fractional reserve banking, but not depression like scenarios of rapid credit contraction as the money multiplier work in reverse. This is unfortunately a very very deep rabbit hole side issue that requires a 30 page essay to get through. In China, which is probably more capitalist than the U.S, they have a different system. They have tons of companies that have bad debts and the government prints money out of thin air to selectively bail them out without austerity forced on the taxpayer, which is why they haven't had a credit crunch that has predicted every year for the last 30 years.

* The happy path of the future AI automation is normal people get access to these robots and use them to produce unlimited prosperity. The bloody path is only the elite get access and they decide to wipe out everyone else with killer robots because they find them to be irritating useless eaters.

[1] https://en.wikipedia.org/wiki/Deep_ecology#Development