How do ZFS snapshots compare to LVM snapshots? Question not specifically for, but anyone who might know something about this.
Using them for system updates/upgrades is built right into FreeBSD (copying a feature from Solaris):
* https://www.freebsd.org/cgi/man.cgi?beadm
If the changes fail just rollback the system to the previous state/snapshot (including kernel changes) via the boot loader.
Services like rsync.net allow one to have offsite backups with easy, and the destination can be encrypted such that the remote end can't see your data. All through an SSH pipe.