In other words, if you give this as advice to someone random, will they end up successful or an outcast. I'd guess the latter in most cases.

The whole thing reads like a fairly standard (but very disorganized) self-help tract trying to exhort people into being more agenty and strategic. Some of it maps directly onto LW self-help posts, even, like 'people are not automatically strategic' and existing techniques like COZE.

Since, for better or worse, most self-help material doesn't wind up helping or harming even when someone actually tries to use them, I don't think that this particular self-help tract will be any different - anyone trying to use the ideas and aspire to be a chef rather than a cook will wind up probably in the same place as they would before. People aren't going to either become billionaires or homeless just because they read something online; if writing could reliably have that sort of impact, we would live in a very different and much more interesting world than we do...

I agree with OP that most people do have sub-optimal levels of agentiness and planning and have really wacky evaluations of risk (consider anything to do with children, or terrorism), so if it did do anything, it would probably be helpful on net.