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Sure, let's use extreme examples.

You wouldn't consider the market decline in 2007-2009 to be an extreme case? Only the 1929 crash was worse.

That is, when I said:

[My retirement community] had a lot of people hit [the "I can't afford retirement"] phase in 2008 and 2009, after the market collapsed.

...I was told they "retired without enough money". But it was an extreme case that affected them. Anyone pushing the envelope got squashed. What were the odds?

And, such crashes have long-term fallout as well, because people become fearful of the market and avoid it. Thus missing out on the recoveries we have seen (so far). In 2007, people were also not fearful of going overly in debt on real estate, not only because they could, but also because they were fed the line that "real estate values have never failed"...
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