The website does work when I enable cookies, and it says he sold his apartment for much more than the median price. I think it also supports the claim that after buying a house, he had a profit left of roughly 10 percent of that house's value (the amount of equity he supposedly said he wouldn't mind losing post-purchase).

Your general argument seems to misrepresent Taleb. Again, we have here a case of someone doing pretty well by focusing on the predictions you can make. (His profit was likely sub-optimal, but that sounds like an example of a prediction you can't make.) And hedging can indeed protect you against the events you keep weirdly suggesting are useless to think about.