(1)
As time goes by, the present becomes the past.
History is a collection of past events.
As more current events occur and develop and eventually become history, history grows and expands.
So history is a good but far from a perfect indicator of the future because history itself keeps changing.
(2)
Like the author says, calamity will continue to happen in financial markets. At what time and in what fashion we can't know for sure. So it's important to protect oneself on the downside. Peace of mind and lack of anxiety are necessities of a happy life. And a lower expectation would help achieve that.
Dow 36,000 still in the cards but probably not so soon...