Ditto here; upgrades are very boring under OpenBSD. You can keep the same setup for ages,
even more with cwm, xterm, mupdf, mpv and a bunch of CLI/TUI tools and games...
The only thing I hate about how boring OpenBSD upgrades are is that I often forget that there are new features I could be exploiting for my server configs. Everything works too smoothly so I'm rarely (if ever) forced to dive into the docs to fix things.