This is very odd:

Initializing machine ID from D-Bus machine ID.
Adding group `systemd-journal' (GID 120) ...
Done.
You are required to change your password immediately (root enforced)
chfn: PAM: Authentication token is no longer valid; new one required
adduser: `/usr/bin/chfn -f systemd Time Synchronization systemd-timesync' 
returned error code 1. Exiting.
dpkg: error processing package systemd (--configure):
 subprocess installed post-installation script returned error exit status 1

I'm not sure if digitalocean images are customized, in a way that
prevent upgrades. Can you try creating system systemd-timesync user, and
re-attempting the upgrade?

$ sudo adduser --quiet --system --group --no-create-home --home /run/systemd \
    --gecos "systemd Time Synchronization" systemd-timesync

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https://bugs.launchpad.net/bugs/1733468

Title:
  do-release-upgrade failed to update to systemd 229-4ubuntu21

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