It would be impossible for a daemon to categorize its users into those two groups and decide when to stop itself from running because it cannot see months into the future.

The scheme I outlined doesn't ask anyone to look into the future. It asks that the service look into the past.

I would argue that it is a trade-off.

Argue if you want—it seems you're predisposed to it. I said it's not an inherent trade-off. The developers/package maintainers are certainly making a trade-off. That's not the same thing as that trade-off being unavoidable.