I absolutely agree. I run FreeBSD on my NAS to take advantage of ZFS but every time I update it I have to Google the process or find my notes since it's incredibly non-intuitive.
At this point, I've only got two services (postgresql and mosquitto) which run on bare metal, everything else is in VMs. Once I move those off of FreeBSD the upgrade process will be greatly simplified (well, as simplified as FreeBSD gets anyway).