In modern times, point releases tend to be about once a year, which doesn't seem too frequent to me? But if you use pkg, and the new point release added a syscall, you will have problems installing new packages (or upgrading) once the package builders update; I don't quite remember the timeline, but it's usually a few months after the point release. (Although, I think there was a time where pkg would default to a faster updating repository, and you might see problems sooner)
My upgrade process is a bit laborious (freebsd-update -r ... upgrade; freebsd-update install; shutdown -r now; freebsd-upgrade install; pkg update; pkg upgrade; reboot). Might be another pkg command I forgot, but it will likely prompt you.
If you're not interested in upgrading everything together at once, ports is probably a better choice. Sometimes after an OS upgrade, you'll need to install a compat port to continue to run old software; it's possible to do that with pkg, but IMHO, it's difficult to get the compat package installed without upgrading other packages, and then you may as well upgrade everything.
Personally, I don't find docker-compose simple. Probably from lack of experience, but I find it hides so much that makes it much more difficult to debug. Most of the time, I'd rather run everything in a single host, but I'm encouraged to use docker-compose by my workplace, so...