Yes, the money flows uphill. Having more wealth means being able to make more wealth, faster. It's a feedback loop. True, some of that comes from printing money. But value is actually being created all the time (which means some new money must be printed all the time), and capital will capture an ever-increasing share of the increasing pie. The rate of this increase is faster than the wealth is created. You can see this in the widening income growth gap between the top and the bottom. In turns out that a rising tide can indeed raise all boats, but it raises the boats at the top of the income curve much faster than those at the bottom, to the point where the boats at the bottom are only infinitesimally better off while the income of the rich is multiplied many times over.

The arc of the U.S. economy over the last 80 years contradicts your position. There has been reduced regulation since the Reagan administration, and also reduced competition. A few blips when internet companies "disrupted" an existing industry, but those industries fairly quickly consolidated on a small group of players.

You're describing regulatory capture, which is true in unregulated capitalism. When I say "unregulated capitalism", I'm not talking about business regulation---I'm talking about regulating capital itself. In a healthy, regulated capitalist system, the political influence of individual companies is diluted and there is greater competition. Business regulation is always needed to ensure things like public safety, contract enforcement, and fair competition. But when disproportionately large players politically capture the regulatory machinery, they tilt the regulatory playing field towards themselves. This is a symptom, it is not the disease.

I'm not really familiar with this nomenclature, the left-anarchists I know generally consider themselves "libertarian" or "market" socialists (or just “anarcho-socialists””). I'm definitely interested to understand your point a bit further; good you point me to some left-anarchist thought around communism vs. socialism?

> Socialism by definition is where the means of production cannot be individually owned

Possibly we're familiar with different strains, but my understanding is that it's less about what's individually/collectively owned and more about the relationship between the person doing the labor and the tools they're using to do that labor (ie. "do the workers own the factory or not?"). Social ownership of means of production is one proposal to achieve "workers owning the factory", but AFAIR there are alternatives.

Even granting that a central enforcement authority must exist, it's not clear to me why that enforcement implies planning. It seems to me that one could have a voluntary cooperative agreement with "town council" style enforcement of property relations (or even something like community-ownership with citizen equity), but still have unregulated trade and barter between cooperative members, or with entities outside the cooperative.

> socialist in a different context (as an ideology) may engender this in contradictory fashion.

I think it's important to also note that there isn't really a central socialist tradition; even at the outset of the movement there were disagreeing views on what properly constituted "socialism" or not. This does't mean that the internal belief systems of these traditions have some inherent contradiction, just that there are multiple paths one might take to similar conclusions, and that these don't always line up 100% when you zoom in on the details.

Your definition of Socialism is pretty narrow. The traditional definition basically just boiled down to "a system where the workers are in charge of their production", which encompasses a lot more ideologies and economic systems than just "everything is owned by everyone", Marxist style.

On the other hand, you're applying a much broader definition of "means of production" than is typically discussed in Socialist circles. Most Socialists don't have any significant issue with personal possessions, or the presumption of exclusive use of things that you consistently are using. The bigger concern for Socialists is rent-seeking on said right of exclusive use.

Basically, only a small subset of Socialists would have any issue with "that's Bob's hammer, don't use it without asking". Most Socialists would be opposed to "that's Bob's hammer, you can't use it unless you toss him a fiver".

An Anarchist commune is approximately peak Socialism, everything else is an (arguably) necessary compromise with the complexities of large scale society.