Red Hat (Enrerprise Linux) & HashiCorp (Terraform) closed the source of their products in different ways, also fucking over their community of clients and contributors, though their reasoning seems slightly more sane than "no more free money, aaargh!"

The "paper billionaire" argument does not hold: https://github.com/MKorostoff/1-pixel-wealth/blob/master/THE_PAPER_BILLIONAIRE.md

To Nole Skum it is a joke. He has a total wealth of about $270 billion. $250 million is approxinately 1/1000 of that.

So divide your wealth by 1000, think of how you would feel losing that due to a rare event, while you knowingly took the risk. Does not seem like a big deal to me at all.

How does the connectivity work? Is there some sort of Cloudflare-like VPN-ish gateway that they host?

Depends on your point of view, you could argue that's just the delivery costs.