Ok, but some more thoughts:

- Regarding: apt-cache policy rsyslog; rsyslogd -version
make sure you're on '8.2001.0-1ubuntu1.1' package level (and not on 
8.2001.0-1ubuntu1)
$ apt-cache policy rsyslog | grep Installed
Installed: 8.2001.0-1ubuntu1.1
(from the logs I can only see 'v8.2001.0' which is reported in both cases - I 
believe)

- with that also make sure the latest logrotate package is installed:
$ apt-cache policy logrotate | grep Installed
Installed: 3.14.0-4ubuntu3

- Just to double check: did you ran 'systemctl status syslog' at a point where 
the syslog was no longer working?
if not please provide the output of this in case syslog stopped working

- Were user, group and/or other permissions changed, check/compare:
$ ls -ld /var/log/
drwxrwxr-x 11 root syslog 4096 Sep 22 16:27 /var/log/
$ ls -la /var/log/syslog
-rw-r----- 1 syslog adm 5598 Sep 29 07:05 /var/log/syslog

- Was the rsyslog configuration changed?
according to your previousmsg the config looks like the (unchanged) default 
config
(anyway, a quick rsyslog config validation can be done with: rsyslogd -N1)

- Do you have selinux installed and enabled ? (/usr/sbin/sestatus)

- Did the time (or TZ) of the system changed in anyway?
"rsyslog no longer stops receiving messages after system time change" 
https://bugzilla.redhat.com/show_bug.cgi?id=1088021

- Is someone/something sending signals to rsyslog (in addition to logrotate)?
I see msgs like "rsyslogd was HUPed" -- it could just be caused by a normal 
logrotate, but if not: according to the rsyslogd mane page: "HUP    This lets 
rsyslogd perform close all open files."

- Could you run the following sequence:
  - systemctl status syslog.service
  - sudo logrotate --force --verbose /etc/logrotate.conf
  - logger -e "Test Error"
  - journalctl  --no-pager | grep "Test"
    Sep 29 06:38:40 s1lp15 ubuntu[206083]: Test Error
  - systemctl status syslog.service

- Potential systemd problems could be found with: grep -i systemd
/var/log/syslog

- I guess you already checked for syslog unit issues in the journal:
journalctl -u syslog.service

- If all this will not provide more indications about what might have
happened, I guess rsyslog in debug mode could be a next step
(https://www.rsyslog.com/doc/v8-stable/troubleshooting/debug.html)

** Bug watch added: Red Hat Bugzilla #1088021
   https://bugzilla.redhat.com/show_bug.cgi?id=1088021

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https://bugs.launchpad.net/bugs/1896575

Title:
  [UBUNTU 20.04] syslog daemon stop running unexpectedly

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