> So I won’t get the helpful message if I happen to go more than a month between system updates. Which I think is a fairly generous window.

Gentoo was my first Linux distro and it was cool.. It definitely taught me a lot about app building. But the expectation that every machine needs to be continuously updated at least once per month is what caused me to go to Debian. You have that server which just works and you haven't logged in there for three months.. or a laptop which you only use for travel? Prepare for broken automated updates and careful package rebuilding in just the right order.