The upgrade failed, in your logs, you have:
"/etc/kernel/postinst.d/initramfs-tools:
update-initramfs: Generating /boot/initrd.img-5.2.0-15-generic
I: The initramfs will attempt to resume from /dev/sda2
I: (UUID=bf02ddd4-8d65-40d6-ab24-4fc8a5673dc6)
I: Set the RESUME variable to override this.
/etc/kernel/postinst.d/zz-update-grub:
Sourcing file `/etc/default/grub'
Sourcing file `/etc/default/grub.d/init-select.cfg'
Generating grub configuration file ...
Found linux image: /boot/vmlinuz-5.2.0-15-generic
Found initrd image: /boot/initrd.img-5.2.0-15-generic
Found linux image: /boot/vmlinuz-5.0.0-27-generic
Found initrd image: /boot/initrd.img-5.0.0-27-generic
Found linux image: /boot/vmlinuz-5.0.0-25-generic
Found initrd image: /boot/initrd.img-5.0.0-25-generic
cannot open 'This': no such pool
run-parts: /etc/kernel/postinst.d/zz-update-grub exited with return code 1
dpkg: error processing package linux-image-5.2.0-15-generic (--configure):
 installed linux-image-5.2.0-15-generic package post-installation script 
subprocess returned error exit status 1
Processing triggers for dbus (1.12.14-1ubuntu2) ...
Processing triggers for initramfs-tools (0.133ubuntu10) ...
update-initramfs: Generating /boot/initrd.img-5.2.0-15-generic
I: The initramfs will attempt to resume from /dev/sda2
I: (UUID=bf02ddd4-8d65-40d6-ab24-4fc8a5673dc6)
I: Set the RESUME variable to override this.
Processing triggers for libgdk-pixbuf2.0-0:amd64 (2.39.2-3) ...
Processing triggers for rygel (0.38.1-2ubuntu2) ...
Errors were encountered while processing:
 zfsutils-linux
 zfs-initramfs
 friendly-recovery
 zfs-zed
 grub-pc
 linux-image-5.2.0-15-generic
Log ended: 2019-09-09  01:10:12"

See the "cannot open 'This': no such pool" while updating grub. This is
why you have kernel 5.0 after it and don't have latest zfs after
upgrade.

You mentionned multiple times a "custom" grub script, does it have
"This" somewhere? We don't have any "This" in the distribution script.

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Packages, which is subscribed to zfs-linux in Ubuntu.
https://bugs.launchpad.net/bugs/1843222

Title:
  Old Linux version booted after upgrade to Ubuntu 19.10

Status in zfs-linux package in Ubuntu:
  New

Bug description:
  I have a triple boot with the following systems:
  - Xubuntu 19.10 from zfs 0.8.1
  - Ubuntu Mate 18.04.3 from zfs 0.7.12
  - Ubuntu 19.10 from ext4

  Upgrading the first system Xubuntu to 19.10 worked fine and I was very happy 
with the almost perfect result and the nice grub-menu.
  Upgrading to Ubuntu 19.10 created the following problems:
  - That system booted after the upgrade to Ubuntu 19.10 in Linux 5.0 with zfs 
0.7.12
  - All grub entries with the ZFS systems disappeared and the whole nice 
grub-menu was gone.

  Running update-grub and grub install; I did see the Linux 5.2 version
  appear, but it still booted from 5.0.

  There were some error messages about mounting/importing during the zfs
  part of the upgrade, but they were the same as the ones during the
  Xubuntu upgrade and that upgrade worked perfectly.

  ProblemType: Bug
  DistroRelease: Ubuntu 19.10
  Package: zfsutils-linux 0.8.1-1ubuntu11
  ProcVersionSignature: Ubuntu 5.0.0-27.28-generic 5.0.21
  Uname: Linux 5.0.0-27-generic x86_64
  NonfreeKernelModules: zfs zunicode zavl icp zcommon znvpair
  ApportVersion: 2.20.11-0ubuntu7
  Architecture: amd64
  CurrentDesktop: ubuntu:GNOME
  Date: Mon Sep  9 01:37:21 2019
  InstallationDate: Installed on 2019-03-10 (183 days ago)
  InstallationMedia: Ubuntu 18.04.2 LTS "Bionic Beaver" - Release amd64 
(20190210)
  SourcePackage: zfs-linux
  UpgradeStatus: Upgraded to eoan on 2019-09-09 (0 days ago)
  modified.conffile..etc.sudoers.d.zfs: [inaccessible: [Errno 13] Permission 
denied: '/etc/sudoers.d/zfs']

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