Upgrades are not that bad. I used to also think the same as you, because the documentation is pretty extensive, and I was used to Windows/MacOS "click here to install updates" process.
But in practice, upgrading OpenBSD is basically:
1) Download and boot the bsd.rd for the new version.
2) Select [U]pgrade when prompted.
3) Mostly just accept defaults on the rest of the prompts. Do read carefully however.
After rebooting, run sysmerge(8). This has actually gotten even easier recently as you no longer need to point it to etc.tgz and xetc.tgz for that release.
If you have any packages installed, run pkg_add -u. If anything goes wonky, you might need to run pkg_check to clean up dependencies.
If you have compiled anything else from source you will need to remake/reinstall that also.
It's definitely more "hands on" than Windows, Mac OS, or most Linux distros. But really not bad.
But in practice, upgrading OpenBSD is basically:
1) Download and boot the bsd.rd for the new version.
2) Select [U]pgrade when prompted.
3) Mostly just accept defaults on the rest of the prompts. Do read carefully however.
After rebooting, run sysmerge(8). This has actually gotten even easier recently as you no longer need to point it to etc.tgz and xetc.tgz for that release.
If you have any packages installed, run pkg_add -u. If anything goes wonky, you might need to run pkg_check to clean up dependencies.
If you have compiled anything else from source you will need to remake/reinstall that also.
It's definitely more "hands on" than Windows, Mac OS, or most Linux distros. But really not bad.