That's really scary, man. What if the system tries to reboot and crashes on the way back up?

It's happened to me before.

Go reboot that damn thing!

The last time it rebooted was due to a power glitch at the data center. Came back up just fine. Prior to that, uptime was over 1,000 days :-)

You don't understand his point.

He's saying, how do you know that the system hasn't acquired some sort of configuration/software/hardware degradation in the meantime that only manifests on boot?

If you don't regularly exercise/test a critical function, then you substantially increase your risk that the critical function will fail when you really do need it.

Q: What's the worst time to find out your system won't boot? A: Right after it crashed.

You are better off with scheduled maintenance periods where you can reboot the server and it isn't critical if it fails. That gives you a chance to correct anything on your terms rather than fire-fighting.

Compare Crash-Only Software (https://en.wikipedia.org/wiki/Crash-only_software or https://lwn.net/Articles/191059/).

So that it crashes now? ;-)

That'll crash it when he has the time to look into it, and has backup handy. Not at a random time.