> nor the stop the world updates that take entirely too long

Interesting enough, that beyond release upgrades, happening may be once a year, all or may be 99% of updates took ~5 minutes of interruption of me, including needed reboot. I really wonder how others manage to have "entirely too long" updates.

5 minutes is too long. My Debian systems never demand that I update them. When I update them, it never even takes two minutes.

That can't be helped. I go for a smoke and when come back system is already upgraded.

I've not being using Debian setups lately, but on Ubuntu, alert on need-to-reboot packages after daily unattended upgrades run is happening almost every month. I'm kinda sure that Debian is on similar schedule here.