Using your reproducer, I see the normal, expected behavior:

nr@seven:~$ systemd-run \
  --unit=test-journal \
  --property=StandardOutput=journal \
  /bin/sh -c 'echo stdout; echo stderr >&2'
Running as unit: test-journal.service; invocation ID: 
c14947d9082b4e6b870f4216d04ee03f
nr@seven:~$ journalctl -u test-journal.service
Jul 13 09:03:44 seven systemd[1]: Started test-journal.service - [systemd-run] 
/bin/sh -c "echo stdout; echo stderr >&2".
Jul 13 09:03:44 seven sh[105158]: stdout
Jul 13 09:03:44 seven sh[105158]: stderr
Jul 13 09:03:44 seven systemd[1]: test-journal.service: Deactivated 
successfully.
nr@seven:~$ apt policy systemd
systemd:
  Installed: 259.5-0ubuntu3
  Candidate: 259.5-0ubuntu3
  Version table:
 *** 259.5-0ubuntu3 500
         75 http://us.archive.ubuntu.com/ubuntu stonking/main amd64 Packages
        500 http://us.archive.ubuntu.com/ubuntu resolute/main amd64 Packages
        100 /var/lib/dpkg/status


Do you have some configuration changes for journald.conf or system.conf? I.e., 
can you share the output of:

systemd-analyze cat-config systemd/system.conf
systemd-analyze cat-config systemd/journald.conf

** Changed in: systemd (Ubuntu)
       Status: New => Incomplete

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https://bugs.launchpad.net/bugs/2160529

Title:
  systemd services with StandardOutput=journal produce no journal
  entries while syslog logging still works

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