Since Sergio mentioned groovy, this really only is a xenial issue:

Test:
1. install dnsqmasq+squid
2. ensure dnsmasq is able to run (port collision >=Focal)
3. stop/start dnsmasq in a loop

for i in $(seq 1 4); do date; echo "-"; systemctl stop dnsmasq; date;
echo "+"; systemctl start dnsmasq; date; done

Xenial: slow
Bionic: fast
Focal: fast
Groovy: fast

Xenial:
Wed Sep  2 06:24:15 UTC 2020
-
Wed Sep  2 06:24:15 UTC 2020
+
Job for dnsmasq.service failed because a timeout was exceeded. See "systemctl 
status dnsmasq.service" and "journalctl -xe" for details.
Wed Sep  2 06:25:46 UTC 2020
Wed Sep  2 06:25:46 UTC 2020
-
Wed Sep  2 06:25:46 UTC 2020
+
Wed Sep  2 06:25:47 UTC 2020
Wed Sep  2 06:25:47 UTC 2020
-
Wed Sep  2 06:25:47 UTC 2020
+
Job for dnsmasq.service failed because a timeout was exceeded. See "systemctl 
status dnsmasq.service" and "journalctl -xe" for details.
Wed Sep  2 06:27:18 UTC 2020
Wed Sep  2 06:27:18 UTC 2020
-
Wed Sep  2 06:27:18 UTC 2020
+
Wed Sep  2 06:27:18 UTC 2020


So as the bug was already flagged, this is really only a xenial issue anymore.
And the fact that it is "ok" for squid to take 30 second for a restart is 
intentional as outlined above.

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https://bugs.launchpad.net/bugs/1761096

Title:
  dnsmasq starts with error on Ubuntu Xenial amd64 when squid installed

Status in dnsmasq package in Ubuntu:
  Fix Released
Status in squid package in Ubuntu:
  Fix Released
Status in dnsmasq source package in Xenial:
  Confirmed
Status in squid source package in Xenial:
  Confirmed

Bug description:
  Setup to reproduce:

  Ubuntu Xenial amd64 net install iso from
  http://archive.ubuntu.com/ubuntu/dists/xenial/main/installer-
  amd64/current/images/netboot/mini.iso

  Install system with mostly defaults + LVM + OpenSSH server

  Note that this bug applies to both DHCP and static IP+DNS network
  configurations

  Once server rebooted and is available, log in and install dnsmasq + squid:
  apt-get update && apt-get install squid dnsmasq

  output of this can be found at https://pastebin.com/9Atuipju
  journalctl -xe output at https://pastebin.com/uLhfM4jN

  Furthermore at this point I can run alternating errors

  root@ubuntu-min:~# date ; service dnsmasq start ; date
  Wed Apr  4 09:18:07 CEST 2018
  Wed Apr  4 09:18:07 CEST 2018
  root@ubuntu-min:~# date ; service dnsmasq stop ; date
  Wed Apr  4 09:18:39 CEST 2018
  Wed Apr  4 09:18:39 CEST 2018
  root@ubuntu-min:~# date ; service dnsmasq start ; date
  Wed Apr  4 09:19:10 CEST 2018
  Job for dnsmasq.service failed because a timeout was exceeded. See "systemctl 
status dnsmasq.service" and "journalctl -xe" for details.
  Wed Apr  4 09:20:40 CEST 2018
  root@ubuntu-min:~# date ; service dnsmasq start ; date
  Wed Apr  4 09:42:57 CEST 2018
  Wed Apr  4 09:42:57 CEST 2018
  root@ubuntu-min:~# date ; service dnsmasq stop ; date
  Wed Apr  4 09:43:14 CEST 2018
  Wed Apr  4 09:43:14 CEST 2018
  root@ubuntu-min:~# date ; service dnsmasq start ; date
  Wed Apr  4 09:43:26 CEST 2018
  Job for dnsmasq.service failed because a timeout was exceeded. See "systemctl 
status dnsmasq.service" and "journalctl -xe" for details.
  Wed Apr  4 09:44:56 CEST 2018

  and so on... Each and every 1 out of 2 stop/start cycle fails in 1m30s
  timeout

  Complete journalctl -xe output attached

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