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It's hard for me to understand how a domain can really be worth large sums of money, when slight variations on spelling or word choice can be just a dozen dollars/year. Maybe in the 90s people would search by domain (e.g. pets.com), but now people find things through search engines.

Can anyone point to examples where a specific domain name measurably paid off?

I would say its become a new way to brand your business by being <commonWord>.com - aka booking.com, reputation.com - In the same way '1-800-GOT-JUNK' is both the brand and the way to access the service.
Rarity. Like paintings.

No one monetized painting by selling tickets to watch it. Yet price goes up. For some - they’re locked in vaults never to be seen.

And price goes up

Since they’re starting some kind of email service, I think it makes a lot of sense to invest in a short and simple domain name. I wouldn’t switch to an email that required me to have a long or hard to explain address.
TLDR; By being famous and offering a lot of money
And no price listed, if that is all you were interested in.
They also used email, zoom and phones!
Who want's to take a wild guess at the purchase price?!
BTW, he says the guy was okay with him revealing the seller's identity, but it wasn't hard to figure out beforehand anyway. I looked up hey.com in one of the DNS resolve history sites, found the old resolver, queried the old resolver which still returned an IP, then hit that IP with a Host: hey.com header and you could still look at the old site :-D Definitely thinking well into six figures on this, with the original declined offer being in the mid five figures.