My (archaeologically informed) value-add thought about the Why Chicago controversy is that the idea that places must continue to exist after their initial purpose has faded should not be taken for granted. Humans have abandoned plenty of places after their purpose expired!

That doesn't mean we have to abandon places, or that we shouldn't let them try to reinvent themselves. But abandonment, even of good-size cities, is a normal and regular thing across much of human history. Maybe we've now got the tools to be an exception.

Also worth noting that the precise opposite is also true in some places. For example, Jericho has been continuously occupied on and off, but mostly on, for something like 9 or 10,000 years.