> I just upgraded my home server from 11.1 to 11.2, now I have to do it again?

You don't have to do anything. As with other software, FreeBSD supports multiple releases. 11.2 is still a supported version, and 11.x will be supported until the year 2021.

See this page for more info: https://www.freebsd.org/security/

> Fortunately, upgrading FreeBSD is a lot more convenient these days than it used to be.

Agreed. freebsd-update has made life so much easier.