> If I run any package manager operations between the mask date and one month after the mask date, I’ll get this comment telling me the package is masked. After a month though, the package will get removed from tree along with the package mask (no need to mask a package which isn’t there anymore). 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.

A month is generous? I mean maybe for my desktop machine. Certainly not for some headless file server.

If you're going more than a month without updating a server, then you should allow for the possibililty of a bit of downtime (or delay to read the docs) when you do get around to updating it. And since it wasn't clear in the article: removing a package from the portage repo doesn't cause the package to be automatically uninstalled from your system, and it doesn't cause the package to be ignored during dependency resolution.

More than a month without an interactive login, sure.