EVEN IF the economy has gotten worse every single year since 2009 (it hasn't) this still leaves the puzzle of why people believed the economy was so strong 2016-2019. The simplest answer is that the number of homeless people you're personally working with is not a reliable macroeconomic indicator
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If the median income in an area with growing population spikes without an increased housing supply, it can be great for ~95% of people but drive the other ~5% out of housing.
There are a LOT of folks who never deal with homeless people.