It most likely needs maintenance. It needs fixing up. This is a deal that Trump used to get on condos.

I'd like to hear more about this. Trump used to buy what? Abandoned condos?

Trump would use his father's $1M loan to buy condos that were undervalued because they were old and in need of fixing. He'd pay people to fix it up and paint it and turn around and flip it for more money. Then with the money he made flipping condos, he started to buy hotels and casinos and made his billions. Of course, he had to eat the costs sometimes and file bankruptcy but he never gave up until he was successful.

My son is learning how to flip houses, a lot of people do this, pay to fix them up and then sell them for more than they bought them for.

Yep, but no one can afford to do that post COVID when their own portfolio isn't filled unfortunately

This blames "remote work", but is there an employer in St Louis that would fill this building with workers as in its heyday?

It’s poor reporting. The sole tenant, AT&T, vacated in 2013/2014 and declined to renew their lease in 2017. Well before the recent remote work trend: https://en.wikipedia.org/wiki/909_Chestnut_Street

I get the sense the city is losing workers, I had an interest in working there once and all I heard from friends were stories of car break-in and general lack of safety.

What motivated you to work there?

After visiting there for a school trip years ago it seemed like a remnant of industrial revolution time. The criminal aspect was doubly disconcerting.

There seem to be a lot of middle-America places that are falling by the wayside because of the functional-person drain. It's not even a brain-drain of white collar people, it's pretty much everyone who wants to live a non-"watch out for your life" lifestyle, which is, everyone?

This has been a St Louis trend for decades. I recall hearing in the mid 2000s how the population was 1/3 that of its its peak in the 1970s.

That said, it is a nice city, and cost of living is (was?) low compared to most other metro centers. I really enjoyed my time in St Louis.