Re: Insured?
That's the beauty of the SpaceX approach - they don't mind testing the limits to find out what is actually viable rather than just theoretically and being conservative with safety margins.
Using their cheap, mass produced starlink satellites in such a situation is worth it - if the launch is a success they get extra resources in-orbit; if not then they've learnt the limits without risking anything that their customers cherish.
Incumbents: it's deemed too risky; delay launch. SpaceX: 9 satellites in orbit & limits learned = success.
(the booster was re-used 6 times and most likely will be used again)