Awesome debugging Martin!

but while I agree that:
  CacheDirectory=pollinate
would in your case mitigate the issue by systemd providing that directory, it 
would also hide that this dir was lost at some point. The postinst of pollinate 
would have created that dir:

root@h:~# grep cache /var/lib/dpkg/info/pollinate.*
/var/lib/dpkg/info/pollinate.postinst:  adduser --disabled-password --quiet 
--system --home /var/cache/$PKG --ingroup daemon --shell /bin/false $PKG
/var/lib/dpkg/info/pollinate.postinst:mkdir -p /var/cache/$PKG
/var/lib/dpkg/info/pollinate.postinst:chown -f $PKG /var/cache/$PKG
/var/lib/dpkg/info/pollinate.postinst:rm -f /var/cache/$PKG/tag

And only on remove it is removed, which didn't happen here:
/var/lib/dpkg/info/pollinate.postrm:    rm -rf /var/lib/$PKG /var/cache/$PKG 
/etc/default/$PKG


And if we examine the groovy image that you referred at 
https://cloud-images.ubuntu.com/daily/server/groovy/current/groovy-server-cloudimg-amd64.img
 it has that path and would therefore not be affected.
Here as example:
$ wget 
https://cloud-images.ubuntu.com/daily/server/groovy/current/groovy-server-cloudimg-amd64.img
...
2021-02-08 16:00:56 (7,71 MB/s) - ‘groovy-server-cloudimg-amd64.img’ saved 
[562692096/562692096]
$ modprobe nbd max_part=8
$ sudo qemu-nbd --connect=/dev/nbd0 /tmp/groovy-server-cloudimg-amd64.img
[sudo] password for paelzer: 
$ sudo fdisk /dev/nbd0 -l
Disk /dev/nbd0: 2,2 GiB, 2361393152 bytes, 4612096 sectors
Units: sectors of 1 * 512 = 512 bytes
Sector size (logical/physical): 512 bytes / 512 bytes
I/O size (minimum/optimal): 512 bytes / 512 bytes
Disklabel type: gpt
Disk identifier: 063C6DF3-80DF-451F-8EA3-60CA46A6188F

Device        Start     End Sectors  Size Type
/dev/nbd0p1  227328 4612062 4384735  2,1G Linux filesystem
/dev/nbd0p14   2048   10239    8192    4M BIOS boot
/dev/nbd0p15  10240  227327  217088  106M EFI System

Partition table entries are not in disk order.
$ mkdir /tmp/imagedisk
$ sudo mount /dev/nbd0p1 /tmp/imagedisk
$ sudo chroot /tmp/imagedisk
root@Keschdeichel:/# ll /var/cache/pollinate/
total 8
drwxr-xr-x  2 pollinate daemon 4096 Feb  7 11:32 ./
drwxr-xr-x 12 root      root   4096 Feb  7 11:32 ../
root@Keschdeichel:/# exit


Could that be an issue in the creation of the cockpit images that you mentioned?
Where could we download one of them to check the state of that path in there?

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https://bugs.launchpad.net/bugs/1848923

Title:
  pollinate.service fails to start: ERROR: should execute as the
  [pollinate] user -- missing CacheDirectory=

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