You're absolutely correct that he sounds like an inevitable broken clock outcome. However, his premise on why and how the last bubble was going to explode, was extremely well supported by argumentation & data. He didn't just say it, he argued it out and supported the premise, and he was right. It wasn't luck, it made perfect sense, and he wasn't the only person using the same argument details.
He's right this time that they've blown another huge bubble in asset values via cheap money / hyper low interest rates. The Fed has finally gotten to the point where they're openly admitting to that (Yellen just did so recently). This is the third time in 20 years they've generated vast asset bubbles with cheap money. Schiff is wrong on the timing because he has persistently underestimated how long the Fed could keep the bubbles inflated via said cheap money.
Raise interest rates just to the average level of the prior 50 years, and see what happens to the housing market.
Yes US will end up losing some of advantages but it doesn't need to be so dramatic. Even in multi polar world with several super powers US will be one of wealthiest and most prosperous countries. The tremendous wealth accumulated over last century is not going anyway.
Wealth follows the wealthy, and most of the wealth in the US rests in very few hands, much of it offshore and in other ways hidden from taxation. If they leave, the "wealth" leaves with them for the most part.
For another nation to get to the level of US it would need all of these things and it would take decades and massive investment to build up all of this. Few very rich people taking their money and leaving for some other country would not be the end of the world.
All true enough, but I'm not convinced the wealthy would leave the US en masse as it gradually declines in power and we enter a more multi-polar world, with the dollar possibly losing reserve status at some point. Where would they go, China? I think in the scenario where the US is less powerful compared to the rest of the world, it's still a very attractive place to live in many ways (edit: especially for Americans).
He's also a gold bug. Other than housing bubble he claims there is a massive bubble in stock market and also that the next crisis will be a currency crisis as people lose confidence in US dollar.
He would probably suggest to invest in gold and in markets outside of US/EU.
Disclaimer: I am not saying I agree with Peter Schiff just describing his view, so please don't down vote me.