Sounds like you probably ran into zfs not being in Debian proper - and buster unlocking dmcrypt, but not being able to mount zfs? Should normally be salvageable via booting previous Jessie kernel and initial ram/root disk (initrd).
At any rate, I gather you've moved on - just sound like an unlucky break - even with root on unsupported zfs.
But then again, the main reason I haven't is because all of my stuff is backed up via Nextcloud, so reinstalling Debian is pretty quick/painless for me.
Zfs encryption was still a bit new, so both boxes uses dmcrypt on full disk plus efi plus /boot (technically redundant, but it works).
Looking forward to hopefully root on encrypted zfs in next Ubuntu lts.
Curious if snapshots can protect you even as far as OS upgrades gone wrong. I'd assume they can, if all filesystems are ZFS + snapshotted.
My issue was that for some reason Linux no longer could find the encrypted partition to decrypt, so I couldn't get it up to a point where I could even work with it.
Your experience has definitely not discouraged me from wanting to ZFS my root partitions though. If only to provide the potential / theoretical ability to roll back a snapshot if necessary!
I can post my "script" when I get home if you want to try it. I use script very liberally, it was my notes of the commands I used in order in order to get ZFS/dmcrypt working.
(open) Zfs now has native encryption:
https://github.com/zfsonlinux/zfs/releases/tag/zfs-0.8.0
(ed: there are some potential benefits to zfs encryption - it's as cross platform as zfs (encrypt an USB drive, use on Linux, os x, windows, freebsd).
Zfs send/receive - receiver can take your encrypted backup - key doesn't have to travel.
Mount drives across dual boot - share encrypted /home between dual boot windows and Linux?
Not sure - but I think volume encryption is supported too. Might simplify encrypted swap (if you already "pay" for zfs). Note: there are apparently some issues with swap on zfs (volumes at least, possibly files too)
If you don't need suspend/resume - suppose you could share one encrypted swap volume across multiboot environments..) )